Methyl 2-bromo-3-nitrobenzoate → Methyl 3-amino-2-bromobenzoate

HRID 51314

Reaction equation

HRID 51314 reaction equation
[H][H].[Br:3][C:4]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]>C(OCC)(=O)C.[Pt]>[Br:3][C:4]1[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 79263Methyl 2-bromo-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 13574117Methyl 3-amino-2-bromobenzoateYield 99%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen gas was passed through a solution of methyl 2-bromo-3-nitrobenzoate (0.20 g, 0.77 mM) and 0.1 g of 3% sulfided platinum on carbon in 25 mL ethyl acetate for 24 hours at room temperature. The catalyst was removed by filtration through celite. Concentration of the filtrate afforded 0.175 g (99%) of methyl 2-bromo-3-aminobenzoate as a yellow oil. 1H NMR (CDCl3) δ7.15 (t, 1H, J=8 Hz), 7.1 (dd, 1H, J=1 and 8 Hz), 6.8 (dd, 1H, J=1 and 8 Hz), and 3.95 (s, 3H). IR (CHCl3, cm−1) 3550, 3380, 2980, 2900, 1729, 1613, 1465, 1451, 1434, 1324, 1266, and 1025. MS (FD) m/e 230, 232.

Workup

  1. customThe catalyst was removed by filtration through celite

Sources & evidence

ORD record
ord-330da4d8e78647319d371684d963957f
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Linked notes

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