HCID 19363214, compound → HCID 19363422, compound

HRID 850470Notes

Reaction equation

HRID 850470 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:12]([O-])=O)[C:4]=1[O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[H][H]>[C].[Pd].C(O)C>[NH2:12][C:5]1[C:4]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 19363214HCID 19363214, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19363422HCID 19363422, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

4-Methoxy-2-nitro-3-pentyloxybenzoic acid (26.8 g, 94.6 mmol) and ethanol (350 ml) were mixed, and 10% palladium-carbon catalyst (2.6 g) was added to this solution. The reaction miture was stirred at room temperature for 7.5 hours in a hydrogen gas stream (3 kgf/cm2) and filtered. The filtrate was concentrated under reduced pressure, and the precipitated crystals were collected by filtration to give 2-amino-4-methoxy-3-pentyloxybenzoic acid (22.7 g, 95%) as gray crystals.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-eae61571449e4e419d76cc50fa0f9e1e
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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