Water → Methyl 4-acetamido-3-hydroxybenzoate

HRID 270124

Reaction equation

HRID 270124 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[C:5]([O:7][CH3:8])=[O:6].[H][H].O.[C:18](OC(=O)C)(=[O:20])[CH3:19]>C1COCC1.[Pd]>[C:18]([NH:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[OH:1])(=[O:20])[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 294866Methyl 3-hydroxy-4-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 22627408Methyl 4-acetamido-3-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A solution of methyl 3-hydroxy-4-nitrobenzoate (0.78 g, 3.96 mmol) in THF (40 ml) with Pd on charcoal (10%, 0.15 g) was stirred in the atmosphere of hydrogen at atmospheric pressure overnight. The mixture was filtered through celite. The solvent was removed in vacuo. The residue was taken into water (20 ml), and acetic anhydride (0.5 ml, 5.29 mmol) was added. The mixture was vigorously stirred at 65° C. for 30 min. After cooling to room temperature, the precipitate was collected by filtration, washed with water, and dried. White powder (0.64 g, 77%).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customThe solvent was removed in vacuo
  3. additionwas added
  4. temperatureAfter cooling to room temperature
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-d16811778448467883d1efc1d438fa79
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Linked notes

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