Kermack, Wm. O.; Wight, Thomas W. published an article in 1935, the title of the article was Attempts to find new antimalarials. XIV. Derivatives of 8-methylquinoline.Product Details of 152626-77-2 And the article contains the following content:
cf. C. A. 29, 7332.6. 5,2-MeO(Me)C6H3NH2, FeSO4, As2O5 and 96% H2SO4, refluxed 4 hrs., give 6-methoxy-8-methylquinoline (I), whose HBr salt, light yellow, m. 268°, and picrate, yellow, m. 232-3°. I in CHCl3, saturated with HBr and treated with Br, gives the 5-Br derivative, m. 116-17° (HBr salt, light yellow, m. 230°). 6-Nitro-m-cresol and Br in CHCl3 give the 4-Br derivative, m. 146°; Me2SO4 and K2CO3 in C6H6 give 4-bromo-6-nitro-m-tolyl Me ether, m. 110-11°; reduction with Fe in concentrated HCl in MeOH gives 4-bromo-5-methoxy-o-toluidine (II), light pink, m. 79-80°; the diazo reaction with CuBr yields 4,6-dibromo-m-tolyl Me ether, m. 73-4°. 6-Bromo-4-nitro-m-tolyl Me ether (III) m. 113-15° (90% yield); reduction gives 90% of 2-bromo-5-methoxy-p-toluidine, m. 71-3° (Ac derivative, m. 130-3°); the Sandmeyer reaction gives III. II with the Skraup reaction gives the 5-Br derivative of I; the 7-Br derivative of I m. 134-5°. 6-Nitro-8-methylquinoline yields a 3-Br derivative, light yellow, m. 188-9°. 8-Bromomethylquinoline, refluxed overnight with N H2SO4, gives 8-quinolylmethyl alc., m. 75-6°; 5-NO2 derivative, light brown, m. 148-9°. 5-Nitro-8-bromomethylquinoline and piperidine in Et2O give the 8-piperidinomethyl derivative, whose HBr salt m. 248-9°. o-O2NC6H4CH2NHEt, Et2NCH2CH2Cl.HCl (IV), K2CO3 and a trace of Cu bronze in C6H6, refluxed 4 hrs., give β-(o-nitrobenzylethylamino)triethylamine (V), whose picrate, light yellow, m. 167-8°; o-NH2 derivative, as the picrate, light yellow, m. 134°; β-(benzylethylamino)-triethylamine picrate, yellow, m. 150-2°. The p-NO2 isomer of V, as the picrate, yellow, m. 195-7°. PrNH2 and IV give β-diethylaminoethylpropylamine, whose picrate, yellow, m. 133-5°; butylamine analog, b. 207-12° (70% yield) (dipicrate, yellow, m. 234°); isobutylamine analog, b. 194-200° (70% yield) (dipicrate, yellow, m. 141°); the following piperidino compounds were analogously prepared; the dipicrates form yellow plates; β-piperidinoethylpropylamine, b. 220-30°, 60% yield (dipicrate, m. 169°); -butylamine, b. 230-40°, 70% (dipicrate, m. 191-2°); -isobutylamine, b. 230-40°, 70% (dipicrate, m. 167-8°); -methylamine, b. 190-200°, 45% (dipicrate, m. 174°); β-piperidinodiethylamine, b. 200-10°, 55% (dipicrate, m. 154°). C2H4Br2 and MeNH2 in EtOH give 50% of sym-dimethylethylenediamine, b. 150-60° (picrate, m. 160°). 8-Bromomethylquinoline and Et2NCH2CH2NHMe with K2CO3 in C6H6 give 8-(β-diethylaminoethylmethylaminomethyl)quinoline, the tri-HBr salt of which m. 215-16°; β-diethylaminodiethylaminomethyl derivative (tri-HBr salt, m. 218-19°; picrate, yellow, m. 131-2°); β-diethylaminoethylpropylaminomethyl derivative (picrate, light yellow, m. 113-15°; dipicrate, deep yellow, m. 163-4°); diethylaminoethylbutylaminomethyl derivative (dipicrate, yellow, m. 178-80°); β-diethylaminoethylisobutylaminomethyl derivative (dipicrate, deep yellow, m. 169-71°); β-piperidinoethylpropylaminomethyl derivative (tri-HBr salt, m. 210°); butylamino analog, m. 211-12°; isobutylamino analog (dipicrate, yellow, m. 210-11°); methylamino analog (dipicrate, yellow, m. 205-6°); β-piperidinodiethylaminomethyl derivative (tri-HBr salt, m. 222°); sym-bis(8-quinolylmethyl)dimethylethylenediamine di-HBr, m. 232°. Bis(8-quinolylmethyl)-β-diethylaminoethylamine, m. 97-8°; picrate, yellow, m. 191°; 8-(β-diethylaminoethylaminomethyl)quinoline tri-HBr, m. 223-4°. 1-β-Bis(8′-quinolylmethyl)aminoethylpiperidine, m. 97-8°; picrate, pale yellow, m. 228-9°. 1,4-Bis(8′-quinolylmethyl)piperazine, with 0.5 mol. H2O, m. 153-4°; HBr salt, m. 265-7°. Although inactive in bird malaria, some of these compounds possess marked local anesthetic activity. The experimental process involved the reaction of 4-Bromo-5-methoxy-2-methylaniline(cas: 152626-77-2).Product Details of 152626-77-2
4-Bromo-5-methoxy-2-methylaniline(cas:152626-77-2) belongs to ethers. Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. Product Details of 152626-77-2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem