Dimethylformamide → 5-Fluoro-2-nitrobenzamide

HRID 1176024Notes

Reaction equation

HRID 1176024 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(=O)C(Cl)=O.C[N:21](C=O)C.[NH4+].[OH-]>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH2:21])=[O:8]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 186681655-Fluoro-2-nitrobenzamideYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 5-Fluoro-2-nitro-benzoic acid (3 g, 16.2 mmol) in 200 mL of methylene chloride was added oxalyl chloride (2.26 g, 17.8 mmol) and a drop of DMF. After stirring for 2 h, the solution was poured into concentrated NH4OH. The partial solution was poured into water, extracted with Ethyl acetate, dried (Na2SO4) and concentrated to give 5-Fluoro-2-nitro-benzamide (2.61 g, 88% yield) used without purification. LCMS m/e 185.1 (M+H) 183.2 (M-H), HPLC tr=2.9 min (100%).

Workup

  1. extractionextracted with Ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-165748cedf7e4997854e02a456cc80fc
Source dataset
uspto-grants-2010_11
Patent number
US07842712B2

Reaction notes

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