Ethyl Acetate → Methyl 6-amino-1,3-benzodioxole-5-carboxylate

HRID 1598978

Reaction equation

HRID 1598978 reaction equation
[N+:1]([C:4]1[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)([O-])=O.C(OCC)(=O)C>[Pd].CO>[NH2:1][C:4]1[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 697581,3-Benzodioxole-5-carboxylic acid, 6-nitro-, methyl ester

Product 1

HCID 290838Methyl 6-amino-1,3-benzodioxole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the methyl 6-nitro-1,3-benzodioxole-5-carboxylate, 5% palladium on carbon (1.5 g), ethyl acetate (180 mL) and methanol (80 mL) was stirred 3 hours under a hydrogen atmosphere (15 psi). The mixture was filtered and concentrated and the residue was recrystallized from cyclohexane (200 mL) to give methyl 6-amino-1,3-benzodioxole-5-carboxylate (6.3 g, 32 mmol), m.p. 107°-108° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue was recrystallized from cyclohexane (200 mL)

Sources & evidence

ORD record
ord-8ccdd3dd60c04b8cbabf949a05640412
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Linked notes

Loading…