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

HRID 330759

反応式

HRID 330759 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 458855Ethyl 3,4-Diaminobenzoate収率 86%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1eb8cd1d69e04211956f80992d8ed9cc
出典データセット
uspto-grants-2014_11
特許番号
US08877707B2

関連ノート

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