N-bromobutanimide → 2-Amino-5-bromo-3-methoxybenzoic acid

HRID 657331Notes

Reaction equation

HRID 657331 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C1C(=O)N([Br:20])C(=O)C1>CO>[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([Br:20])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 454804572-Amino-5-bromo-3-methoxybenzoic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-3-(methyloxy)benzoic acid (15.0 g, 89.7 mmol) in MeOH (100 mL) was added NBS (16.8 g, 94.2 mmol) at −5° C. The reaction was kept stirring at 0° C. overnight, then put into the ice water under the condition of stirring. A precipitate formed and was filtered out using Celite, and dried in vacuo to afford 2-amino-5-bromo-3-(methyloxy)benzoic acid (22.0 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 6.93 (s, 1H), 3.87 (s, 3H).

Workup

  1. stirringof stirring
  2. customA precipitate formed
  3. filtrationwas filtered out
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d5120ef51d464a60a656a86cc59deb28
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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