Tetrahydrofuran → 4,5-Diamino-3-chloro-2-phenylamino-benzoic acid methyl ester

HRID 32033

Reaction equation

HRID 32033 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH2:13])=[C:6]([Cl:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCO.CO.[NH4+].[Cl-].C1COCC1>C(Cl)Cl.C1COCC1.O.[Zn]>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:13])=[C:6]([Cl:14])[C:5]=1[NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 18681192Ethanol, mixt. with methanolHCID 858681964-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester

Product 1

HCID 858681984,5-Diamino-3-chloro-2-phenylamino-benzoic acid methyl esterYield 70.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

4-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester 5c (0.50 g, 1.55 mmol) is dissolved into 2:1 EtOH/MeOH (15.5 mL). Saturated aqueous NH4Cl (15 mL), Zn powder (1.02 g, 15.6 mmol), and THF (10 mL) are added. After stirring for 20 hours, the reaction mixture is diluted with CH2Cl2/THF and water. The organic layer is washed with water (3×). The combined organic extracts are dried (Na2SO4) and concentrated under reduced pressure. The solids are triturated with ether to give 0.32 g (70%) clean desired product.

Workup

  1. washThe organic layer is washed with water (3×)
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe solids are triturated with ether

Sources & evidence

ORD record
ord-0e5849934f384e7db4147f0d080c0160
Source dataset
uspto-grants-2008_09
Patent number
US07425637B2

Linked notes

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