N-(2',4'-difluoro-5-nitrobiphenyl-3-yl)acetamide → N-(5-amino-2',4'-difluorobiphenyl-3-yl)acetamide

HRID 64086Notes

Reaction equation

HRID 64086 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[C:11]([NH:18][C:19](=[O:21])[CH3:20])[CH:10]=1>CO.C(OCC)(=O)C.[Pd]>[NH2:15][C:13]1[CH:12]=[C:11]([NH:18][C:19](=[O:21])[CH3:20])[CH:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:14]=1

Participants

5

Reactant 1

HCID 89500094N-(2',4'-difluoro-5-nitrobiphenyl-3-yl)acetamide

Product 1

HCID 89500067N-(5-amino-2',4'-difluorobiphenyl-3-yl)acetamideYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(2′,4′-difluoro-5-nitrobiphenyl-3-yl)acetamide (4 g, 13.7 mmol) in methanol (30 ml) and ethyl acetate (15 ml) was added 10% Pd/C (400 mg, 0.1 eq.) and the reaction vessel was purged with nitrogen gas for 5 min. The mixture was then hydrogenated with H2 balloon for 12 h. The mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure to afford the compound in 89% yield (3.2 g). 1H NMR (300 MHz, DMSO-d6): δ 9.77 (br s, 1H), 7.46-7.42 (m, 1H), 7.35-7.28 (m, 1H), 7.2-7.15 (m, 1H), 6.99 (br s, 1H), 8.86 (d, 1H), 6.39 (d, 1H), 5.45 (br s, 2H), 2.02 (s, 3H).

Workup

  1. customthe reaction vessel was purged with nitrogen gas for 5 min
  2. filtrationThe mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto afford the compound in 89% yield (3.2 g)

Sources & evidence

ORD record
ord-0bc4441412ac4097a17161710fa057ef
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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