Sodium Hydroxide → 5-aminonaphthalene-2-carboxylic acid

HRID 1089580Notes

Reaction equation

HRID 1089580 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 1N 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-5e931f8baa4643b292abd70aeac44ae0
Source dataset
uspto-grants-1990_10
Patent number
US04966975

Reaction notes

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