Sodium Hydroxide → 8-Aminonaphthalene-2-carboxylic acid

HRID 1089574Notes

Reaction equation

HRID 1089574 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([C:12]([O:14]CC)=[O:13])[CH:8]=[CH:7]2.[OH-].[Na+]>O1CCOCC1>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14696377Ethyl 8-Amino-2-naphthoate

Product 1

HCID 134408878-Aminonaphthalene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

According to the procedure of W. Adcock, et al. Aust. J. Chem. 18, 1351 (1965), a mixture of ethyl 8-amino-2-naphthoate (5.2 g, 0.024 mol), 1N NaOH (48 mL, 0.048 mol), and dioxane (50 mL) was stirred at room temperature for 3 hours. The dioxane was removed under reduced pressure, and the aqueous phase was diluted with H2O (100 mL) and extracted with ether. Neutralization with acetic acid produced a yellow precipitate which was collected by filtration (3.2 g, 71%), m.p. 221°-223° C.

Workup

  1. customThe dioxane was removed under reduced pressure
  2. additionthe aqueous phase was diluted with H2O (100 mL)
  3. extractionextracted with ether
  4. customNeutralization with acetic acid produced a yellow precipitate which
  5. filtrationwas collected by filtration (3.2 g, 71%), m.p. 221°-223° C.

Sources & evidence

ORD record
ord-9a7bc8ebd6fe4245803da867fa9bd0c1
Source dataset
uspto-grants-1990_10
Patent number
US04966975

Reaction notes

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