4-Amino-2-(2-chloro-phenylamino)-3-fluoro-5-nitro-benzoic acid methyl ester → 4,5-Diamino-2-(2-chloro-phenylamino)-3-fluoro-benzoic acid methyl ester

HRID 1767793Notes

Reaction equation

HRID 1767793 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH2:13])=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22]>CC(O)=O.C(OCC)(=O)C.[Zn]>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:13])=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22]

Participants

5

Reactant 1

HCID 865928774-Amino-2-(2-chloro-phenylamino)-3-fluoro-5-nitro-benzoic acid methyl ester

Product 1

HCID 865928784,5-Diamino-2-(2-chloro-phenylamino)-3-fluoro-benzoic acid methyl esterYield 48%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Amino-2-(2-chloro-phenylamino)-3-fluoro-5-nitro-benzoic acid methyl ester 5b (0.30 g, 0.88 mmol) is suspended in AcOH (5 mL) and zinc dust (0.29 g, 4.42 mmol) is added. After 15 minutes, the reaction is complete. The reaction mixture is diluted with ethyl acetate and filtered through Celite. The filtrate is washed with water, saturated NaHCO3, 10% K2CO3 and brine. The organic layer is dried (MgSO4) and concentrated under reduced pressure to give 0.13 g (48%) pure desired product as an whitish brown foam.

Workup

  1. filtrationfiltered through Celite
  2. washThe filtrate is washed with water, saturated NaHCO3, 10% K2CO3 and brine
  3. dry with materialThe organic layer is dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57eba678fd8042b3ac80c6c010a88d5e
Source dataset
uspto-grants-2007_06
Patent number
US07235537B2

Reaction notes

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