Methanol → Methyl 3-amino-4-(2,2-dimethoxyethyl)benzoate

HRID 564967Notes

Reaction equation

HRID 564967 reaction equation
[CH3:1][O:2][CH:3]([O:18][CH3:19])[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-])=O.CO>[C].[Pd].C(O)(=O)C>[NH2:15][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:5]=1[CH2:4][CH:3]([O:18][CH3:19])[O:2][CH3:1])[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 887MethanolHCID 10265064Methyl 4-(2,2-dimethoxyethyl)-3-nitrobenzoate

Product 1

HCID 11053739Methyl 3-amino-4-(2,2-dimethoxyethyl)benzoateYield 106.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixture of 4.40 g (16.3 mmol) of methyl 4-(2,2-dimethoxyethyl)-3-nitrobenzoate in a solvent mixture of 200 ml of methanol and 2 ml of acetic acid was added 0.50 g of 5% palladium-carbon to perform catalytic hydrogenation at ambient temperature under normal pressure and then treat the reaction mixture in a conventional manner. Thus, 4.16 g of methyl 3-amino-4-(2,2-dimethoxyethyl)benzoate was obtained.

Workup

  1. customat ambient temperature
  2. additiontreat the reaction mixture in a conventional manner

Sources & evidence

ORD record
ord-d4c28d2c2fd8407c8f747a75425e1bbf
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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