Methyl 4-(2,2-dimethoxyethyl)-3-nitrobenzoate → Methyl 3-amino-4-(2,2-dimethoxyethyl)benzoate
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
Product 1
Reagents, catalysts & solvents 1
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-amino-4-carbomethoxy-phenylacetaldehyde dimethylacetal.
Workup
- filtrationThe solution was filtered through celite
- customevaporated to an oil
- customCrystallization from ether and hexanes
Sources & evidence
- ORD record
- ord-7eb25fc7878d44a78ab16f81e9413152
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05856517
Reaction notes
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