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

HRID 378371Notes

Reaction equation

HRID 378371 reaction equation
[CH3:1][O:2][CH:3]([O:18][CH3:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][C:6]=1[N+:15]([O-])=O>CO>[CH3:19][O:18][CH:3]([O:2][CH3:1])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][C:6]=1[NH2:15]

Participants

3

Reactant 1

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

Product 1

HCID 11053739Methyl 3-amino-4-(2,2-dimethoxyethyl)benzoateYield 62.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Carbomethoxy-2-nitrophenylacetaldehyde dimethylacetal (8.75 g, 41.43 mmole) was reduced under hydrogen (50 psi, 0.45 g of 10% Pd/carbon) in 170 mL of methanol for 2.5 h. The solution was filtered through celite and evaporated to an oil. Crystallization from ether and hexanes gave 6.16 g of 2-amino4-carbomethoxy-phenylacetaldehyde dimethylacetal.

Workup

  1. filtrationThe solution was filtered through celite
  2. customevaporated to an oil
  3. customCrystallization from ether and hexanes

Sources & evidence

ORD record
ord-2e4cc4ff3fd440cb933a628667e6fc52
Source dataset
uspto-grants-2000_02
Patent number
US06030994

Reaction notes

Loading…