3-Methoxy-N-(1-methylazetidin-3-yl)-4-nitrobenzamide → 4-Amino-3-methoxy-N-(1-methylazetidin-3-yl)benzamide

HRID 1487649Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[C:6]([NH:8][CH:9]1[CH2:12][N:11]([CH3:13])[CH2:10]1)=[O:7]>[Pd].CO.C1COCC1>[NH2:17][C:16]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH:9]2[CH2:10][N:11]([CH3:13])[CH2:12]2)=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-methoxy-N-(1-methylazetidin-3-yl)-4-nitrobenzamide (1 equiv) and 10% palladium on carbon was stirred in a mixture of MeOH/THF under a hydrogen atmosphere. The mixture was stirred at 50° C. for 2 h. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure to give the desired product (99% yield) as a white solid. MS (ESI) m/z 236.1 [M+H]+.

Workup

filtrationThe reaction mixture was filtered
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-ac6b3e1d609543e9afb0779bd720ce5a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428509B2

Reaction notes

Loading…