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ChemicalBook CAS DataBase List Benzaldehyde, 2-amino-5-chloro-3-methyl-
151446-29-6

Benzaldehyde, 2-amino-5-chloro-3-methyl- synthesis

3synthesis methods
-

Yield:151446-29-6 92%

Reaction Conditions:

with manganese(IV) oxide in diethyl ether at 20;

Steps:

2

Preparation 22-Amino-5-chloro-3-methyl-benzaldehyde (3a)[00141 ] To a suspension of MnO2 (10.15 g, 1 16.0 mmol) in dry diethyl ether (100 mL) is added dropwise a solution of (2-amino-5-chloro-3-methyl-phenyl)-methanol (2a) (5.0 g, 29.0 mmol) in diethyl ether (150 mL). The mixture is stirred at rt overnight. Precipitates are filtered off, solvent evaporated and crude product is purified by flash chromatography on silica gel (petroleum ether - DCM, 2: 1 ). The title compound 3a is obtained as a yellow solid (4.60 g, 92%). 1H NMR (400 MHz, CDCI3), δ (ppm): 2.16 (s, 3H); 6.20 (br s, 2H); 7.20 (m, 1 H); 7.35-7.33 (m, 1 H) and 9.80 (s, 1 H).

References:

WO2012/164085,2012,A1 Location in patent:Page/Page column 68