3-Chloro-4-fluoroaniline → N-(4-Fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide

HRID 1189630Notes

Reaction equation

HRID 1189630 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH3:12])[C:8]([N+:13]([O-:15])=[O:14])=[CH:7][C:3]=1[C:4]([OH:6])=O.ClC(N(C)C)=C(C)C.[F:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=1[Cl:32].CCN(C(C)C)C(C)C>C(Cl)Cl>[F:24][C:25]1[CH:31]=[CH:30][C:28]([NH:29][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([N+:13]([O-:15])=[O:14])[C:9]([NH:11][CH3:12])=[CH:10][C:2]=2[F:1])=[CH:27][C:26]=1[Cl:32]

Participants

6

Reactant 4

HCID 97083-Chloro-4-fluoroanilineHCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 595298342-Fluoro-4-(methylamino)-5-nitrobenzoic acid

Product 1

HCID 67957648N-(4-Fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-fluoro-4-methylamino-5-nitro-benzoic acid (0.500 g, 2.34 mmol), (1-chloro-2-methyl-propenyl)-dimethylamine (0.371 mL, 2.80 mmol) and DCM (50 mL) is stirred for 30 min, then 4-fluoro-3-chloro-aniline (0.340 g, 2.34 mmol) and DIPEA (0.549 mL, 3.15 mmol) are added and it is stirred for 2 h. The mixture is concentrated, water is added and the precipitate is filtered, washed with water and dried to give the subtitle compound.

Workup

  1. stirringit is stirred for 2 h
  2. concentrationThe mixture is concentrated
  3. additionwater is added
  4. filtrationthe precipitate is filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-3fc71b1b34534393b9dc014119b84d24
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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