Sodium Hydroxide → 1-Amino-4-bromo-2-naphthoic acid

HRID 82437Notes

Reaction equation

HRID 82437 reaction equation
Br.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([Br:13])=[CH:5][C:4]=1[C:14]([O:16]C)=[O:15].[OH-].[Na+]>C1COCC1>[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([Br:13])=[CH:5][C:4]=1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66979039Methyl 1-amino-4-bromo-2-naphthoate hydrobromide

Product 1

HCID 584318421-Amino-4-bromo-2-naphthoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 1-amino-4-bromo-2-naphthoate hydrobromide (2.00 g, 5.54 mmol) in 20 mL of THF was added sodium hydroxide (11.1 mL, 20% aqueous, 55.4 mmol). The mixture was stirred at 50° C. for 20 h, then heated at 90° C. for 2 h. The solvent was removed in vacuo and hydrochloric acid (1 N aqueous) was added until pH ˜2. The beige solid was collected via filtration, washed twice with water, and dried to provide 1-amino-4-bromo-2-naphthoic acid that gave a mass ion (ES+) of 266.0 (79Br) for [M+H]+.

Workup

  1. temperatureheated at 90° C. for 2 h
  2. customThe solvent was removed in vacuo and hydrochloric acid (1 N aqueous)
  3. additionwas added until pH ˜2
  4. filtrationThe beige solid was collected via filtration
  5. washwashed twice with water
  6. customdried

Sources & evidence

ORD record
ord-1d70321a9b6d4c8d8f80406ccfd472d1
Source dataset
uspto-grants-2014_09
Patent number
US08846702B2

Reaction notes

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