N-(3-dimethylamino-2,2-dimethyl-propyl)-3-methoxy-4-nitro-benzamide → 4-amino-N-(3-dimethylamino-2,2-dimethyl-propyl)-3-methoxy-benzamide

HRID 2234354Notes

Reaction equation

[CH3:1][N:2]([CH3:22])[CH2:3][C:4]([CH3:21])([CH3:20])[CH2:5][NH:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([O:17][CH3:18])[CH:9]=1>CCO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][C:4]([CH3:20])([CH3:21])[CH2:3][N:2]([CH3:1])[CH3:22])=[O:19])=[CH:9][C:10]=1[O:17][CH3:18]

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of N-(3-dimethylamino-2,2-dimethyl-propyl)-3-methoxy-4-nitro-benzamide (Intermediate 23; 5.7 g, 18.40 mmol), 5% Pd on charcoal (569 mg) in EtOH (300 mL) was stirred at 40° C. under a hydrogen atmosphere for 16 h. The reaction mixture was then filtered through celite, washed with copious MeOH and the volatiles removed under reduced pressure to afford the title compound (5.36 g, Quant.) as a foam.

Workup

filtrationThe reaction mixture was then filtered through celite
washwashed with copious MeOH
customthe volatiles removed under reduced pressure

Sources & evidence

ORD record: ord-c80c79f728ad48729456c07f8c630038
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709471B2

Reaction notes

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