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

HRID 1916879Notes

Reaction equation

HRID 1916879 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 458855Ethyl 3,4-DiaminobenzoateYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step a 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.

Workup

  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

Sources & evidence

ORD record
ord-fbaeb59219a0474bb7b7b927848e6b84
Source dataset
uspto-grants-2013_12
Patent number
US08618151B2

Reaction notes

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