Methyl 4-ethoxy-5-methoxy-2-nitrobenzoate → Methyl 2-amino-4-ethoxy-5-methoxybenzoate

HRID 871233Notes

Reaction equation

HRID 871233 reaction equation
[CH2:1]([O:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([N+:16]([O-])=O)[CH:5]=1)[CH3:2].[H][H]>CO.[Pd]>[NH2:16][C:6]1[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:13]([O:14][CH3:15])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 10491210Methyl 4-ethoxy-5-methoxy-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 10489373Methyl 2-amino-4-ethoxy-5-methoxybenzoateYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 4-ethoxy-5-methoxy-2-nitrobenzoate (8.38 g, 32.8 mmol) and Pd/C (10%, 0.85 g) in MeOH (20 mL) was stirred under 1 atmosphere of hydrogen at room temperature for 6 hours. The reaction mixture was filtered with Celite and washed with MeOH. The filtration was concentrated under reduced pressure to give methyl 2-amino-4-ethoxy-5-methoxybenzoate as solid (6.832 g, 92%). 1H NMR (300 MHz, CDCl3) δ 7.30 (s, 1H), 6.13 (s, 1H), 5.56 (br, 2H), 4.08 (q, 2H), 3.85 (s, 3H), 3.82 (s, 3H), 1.48 (t, 3H); LC-MS (ESI) m/z 226 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered with Celite
  2. washwashed with MeOH
  3. filtrationThe filtration
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-ee59adea3d7c41dbb56afdcf4ec54d25
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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