Sodium Hydroxide → 5-aminonaphthalene-2-carboxylic acid

HRID 330514Notes

Reaction equation

HRID 330514 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]([O:14]CC)=[O:13])=[CH:7]2.[OH-].[Na+]>O1CCOCC1>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]([OH:14])=[O:13])=[CH:7]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14696444HCID 14696444, compound

Product 1

HCID 2779485-aminonaphthalene-2-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 5-amino-2-naphthoate (7.0 g, 0.0325 mol), dioxane (40 ml), and 1 N NaOH (39 mL) was stirred at room temperature for 16 hours. The dioxane was removed under reduced pressure, H2O (50 mL) was added, and the mixture was neutralized with acetic acid (2.23 mL). The resulting brown solid precipitate was collected by filtration to give the desired product (5.4 g, 89%), m.p. 231°-234° C.

Workup

  1. customThe dioxane was removed under reduced pressure, H2O (50 mL)
  2. additionwas added
  3. filtrationThe resulting brown solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-a58bfcd8f69744d2834024fe02519817
Source dataset
uspto-grants-1990_01
Patent number
US04897405

Reaction notes

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