2-Fluoro-5-nitrobenzoic acid → 2-Fluoro-N-(3-fluoro-phenyl)-5-nitro-benzamide

HRID 227726Notes

Reaction equation

HRID 227726 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:14][C:15]1[CH:16]=[C:17]([NH3+:21])[CH:18]=[CH:19][CH:20]=1>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([F:14])[CH:16]=1)=[O:6]

Participants

4

Reactant 2

HCID 2809972-Fluoro-5-nitrobenzoic acidHCID 35417393-Fluoro-phenyl-ammonium

Product 1

HCID 433774282-Fluoro-N-(3-fluoro-phenyl)-5-nitro-benzamide

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of 2-Fluoro-5-nitro benzoic acid (1.48 g, 8 mmol) and 3-Fluoro-phenyl-ammonium (920 μl, 8.5 mmol) in methylene chloride/DMF (10:1) 20 ml was added 10 g PS-resin (1.54 mmol/g). The reaction mixture was stirred at room temperature for overnight and then PS-resin was moved by filtration. The filtrate was evaporated to yield the title compound as a yellow solid. (1.11 g, 50%). MS (ESI) m/z=279 [M+H]+. 1H NMR (400 MHz, d6-DMSO) δ 10.89(s, 1H), 8.58-8.47(m, 1H), 7.72-7.67 (m, 1H), 7.45-7.42 (m, 1H), 7.00-6.98 (m, 1H), 6.37-6.28 (m, 2H)

Workup

  1. filtrationPS-resin was moved by filtration
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-2ca6198db18349f3806f5879d8741d93
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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