N-(4-bromophenyl)-2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzamide → 5-amino-N-(4-bromophenyl)-2-(2,2-difluoroethoxy)-4-(methylamino)benzamide

HRID 1410228Notes

Reaction equation

HRID 1410228 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[C:13]([NH:19][CH3:20])=[CH:12][C:11]=2[O:21][CH2:22][CH:23]([F:25])[F:24])=[CH:4][CH:3]=1>[Ni].C1COCC1>[NH2:16][C:14]1[C:13]([NH:19][CH3:20])=[CH:12][C:11]([O:21][CH2:22][CH:23]([F:24])[F:25])=[C:10]([CH:15]=1)[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:26]

Participants

4

Reactant 1

HCID 59529852N-(4-bromophenyl)-2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzamide

Product 1

HCID 595298615-amino-N-(4-bromophenyl)-2-(2,2-difluoroethoxy)-4-(methylamino)benzamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The sub-title compound was prepared by hydrogenation according to procedure 3d using N-(4-bromophenyl)-2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzamide (1.01 g; 2.34 mmol), Ra—Ni (14 mg), H2 (8 atm) and THF (50 mL). Yield: 905 mg (97%).

Sources & evidence

ORD record
ord-b82a13f53e984437b6bfe482039c3a2c
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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