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

HRID 1042297Notes

Reaction equation

HRID 1042297 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][CH3:17])=[O:15].[OH-].[Na+].[OH-].[Li+]>C1COCC1>[BrH:13].[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][CH3:17])=[O:15].[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

6

Reactant 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 66979039Methyl 1-amino-4-bromo-2-naphthoate hydrobromide

Product 2

HCID 584318421-Amino-4-bromo-2-naphthoic acidHCID 66979039Methyl 1-amino-4-bromo-2-naphthoate hydrobromide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 1-amino-4-bromo-2-naphthoate hydrobromide was prepared as described in Example 1. 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). Alternatively, lithium hydroxide could be used. 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-707aede9741c41aab3e8433a80cb266e
Source dataset
uspto-grants-2013_10
Patent number
US08557832B2

Reaction notes

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