2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 3,4-Diaminobenzoate

HRID 330759

반응식

HRID 330759 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1O)C(OC)=O.C([C:15]1[CH:24]=CC(C(OC)=O)=CC=1)=O.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#[N:26].[C:39]([O-:42])(O)=[O:40].[Na+]>CO>[CH2:24]([O:42][C:39](=[O:40])[C:4]1[CH:9]=[CH:10][C:11]([NH2:26])=[C:2]([NH2:1])[CH:3]=1)[CH3:15]

참가 물질

6

반응물 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10815Methyl 3-amino-4-hydroxybenzoateHCID 15294Methyl 4-FormylbenzoateHCID 516892Sodium Bicarbonate

생성물 1

HCID 458855Ethyl 3,4-Diaminobenzoate수율 86%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of methyl 3-amino-4-hydroxybenzoate (2.5 g, 15 mmol) and methyl 4-formylbenzoate (2.46 g, 15 mmol) in methanol (75 mL) was stirred at rt overnight. The solvent was evaporated under reduced pressure and the remaining residue was dissolved in dichloromethane (150 mL). DDQ (3.5 g, 15.4 mmol) was added and the reaction mixture was stirred at rt for 1 h. Saturated NaHCO3 (200 mL) was added. The suspension was filtered off, the resulting solid was washed with saturated NaHCO3 (50 mL), water (50 mL), and ethyl acetate (100 mL) and dried in vacuo to give compound 1 (4 g, 86% yield) as yellow solid.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe remaining residue was dissolved in dichloromethane (150 mL)
  3. stirringthe reaction mixture was stirred at rt for 1 h
  4. filtrationThe suspension was filtered off
  5. washthe resulting solid was washed with saturated NaHCO3 (50 mL), water (50 mL), and ethyl acetate (100 mL)
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-1eb8cd1d69e04211956f80992d8ed9cc
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877707B2

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