Sodium Acetate → Methyl 3-amino-2-hydroxybenzoate

HRID 415166Notes

Reaction equation

HRID 415166 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:13]([O-])=O)[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C([O-])(=O)C.[Na+].[H][H]>C(OCC)(=O)C.O.[Pd]>[NH2:13][C:4]1[C:5]([OH:12])=[C:6]([CH:11]=[CH:2][CH:3]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 3

HCID 517045Sodium AcetateHCID 970238Methyl 5-bromo-2-hydroxy-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 12782444Methyl 3-amino-2-hydroxybenzoateYield 59%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of methyl 5-bromo-2-hydroxy-3-nitrobenzoate (38.4 g, 0.14 mol), sodium acetate (19.63 g, 0.24 mol) and 10% Pd/C (3.84 g) in ethyl acetate (500 mL) and water (30 mL) was stirred at 25° C. under 1 atm of hydrogen for 16 hr. The mixture was filtered and the filtrate was washed with water (500 mL×2), brine (300 mL), dried over anhydrous sodium sulfate and concentrated to give crude product. The crude product was washed with methanol at 0° C. to give methyl 3-amino-2-hydroxybenzoate (13.67 g, yield 59%) as a light yellow solid. 1H-NMR (400 MHz, CDCl3-d) δ 3.88-3.94 (s, br, 2H), 3.91 (s, 3H), 6.70-6.74 (t, J=7.8 Hz, 1H), 6.88-6.90 (m, 1H), 7.24-7.26 (m, 1H), 10.91 (s, 1H); LC-MS (ESI) m/z 168 [M+1]−.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed with water (500 mL×2), brine (300 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto give crude product
  6. washThe crude product was washed with methanol at 0° C.

Sources & evidence

ORD record
ord-dcd6528400ca419a96c4a33788eb2d51
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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