5- Bromo-2-methoxyaniline

Palladium-catalyzed amination has also been used to prepare aminoquinazolines substituted in the benzo ring <2002JA1594, 2003TL7533>. The reactions were peformed on solid support and involved amination of all four chloro isomers with 4-methoxyaniline <2002JA1594>, or the amination of 6-bromo or 6- or 7-chloroquinazoline derivatives with a variety of aliphatic amines <2003TL7533>. 

Problem 19.28 Prepare (a) 2-bromo-4-hydroxytoluene from toluene, (b) 2-hydroxy-5-methylbenzaIdehyde from p-toluidine, (c) m-methoxyaniline from benzenesulfonic acid. M... 

Work on the electrodiemical oxidation of 2-aminopolylluorodiphei I-amines (see Vol. 1, p. 211) has been extended to the bromo- and methoxy-compounds (199), synthesized via the attack of lithium pentafluoroanilide on the corresponding 2-X- and 4-X-tetrafluoronitrobenzenes. Electrochemical oxidation yields the corresponding phenazines (200 Z = F), and hexafluoro-2,7-dimethoxyphenazine (200 X = F, Y = Z = OMe) is obtaiiKd similarly from 2,3,S,6-tetrafluoro-4-methoxyaniline. Octafluorophenazine (200 X =... 

Bromo-3-ethoxypyridine, in B-60275 2-Bromo-3-methoxyaniline, in A-70099 2-Bromo-3-methoxy-6-methylpyridine, in B-60267... 

Condensation of l-bromo-2-methoxy-4-methyl benzene (64) with 5,6-dimethoxyaniline acetate (65) in pyridine in the presence of Cu and K2CO3 and subsequent hydrolysis with 20% KOH furnished the di-phenylamine derivative (66) which on treatment with palladium acetate in DMF afforded murrayastine (13). Condensation of l-bromo-3-methoxy-4-methylbenzene (67) with the dimethyl acetal of 6-formyl-5-methoxyaniline acetate (68) furnished the diphenylamine derivative (69) which on hydrolysis and on subsequent cyclisation furnished murray-aline (14). 

---