Methyl 3-hydroxy-2-nitrobenzoate → Anthranilic acid, 3-hydroxy-, methyl ester

HRID 415163Notes

Reaction equation

HRID 415163 reaction equation
[OH:1][C:2]1[C:3]([N+:12]([O-])=O)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]>C(OCC)(=O)C.[Pd]>[NH2:12][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 13659833Methyl 3-hydroxy-2-nitrobenzoate

Product 1

HCID 205248Anthranilic acid, 3-hydroxy-, methyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of methyl 3-hydroxy-2-nitrobenzoate (14 g, 71 mmol) and 10% Pd/C (1.4 g) in ethyl acetate (300 mL) was purged in 1 atm hydrogen and stirred at 25° C. for 4 hr. The mixture was filtered, and the filtrate was concentrated to give methyl 2-amino-3-hydroxybenzoate (11.5 g, yield 97%) as a light yellow solid. 1H-NMR (400 MHz, CDCl3-d) δ 3.88 (s, 1H), 5.84 (s, br 3H), 6.50-6.54 (t, J=8.0 Hz, 1H), 6.84-6.86 (d, J=7.2 Hz, 1H), 7.47-7.49 (d, J=7.6 Hz, 1H); LC-MS (ESI) m/z 168 [M+1]+.

Workup

  1. customwas purged in 1 atm hydrogen
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d4b463cc75aa49979b9fc7625e479361
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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