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

HRID 217071

반응식

HRID 217071 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 21919333Tetrahydrofurane dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5578053e37d0426f97e5645bfe047a76
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193231B2

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