Formic Acid → Ethyl α-amino-6-methoxy-2-naphthaleneacetate

HRID 1154537Notes

Reaction equation

HRID 1154537 reaction equation
O[N:2]=[C:3]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(O)=O>CO.[Zn]>[NH2:2][CH:3]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 73678899HCID 73678899, compound

Product 1

HCID 20433914Ethyl α-amino-6-methoxy-2-naphthaleneacetateYield 61.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

2-Bromo-6-methoxynaphthalene was converted to the 2-lithio derivative by reaction with n-butyllithium. Diethyl oxalate was then reacted with the 2-lithio-6-methoxynaphthalene to afford ethyl α-keto-6-methoxy-naphth-2-ylacetate. The latter compound was reacted with hydroxylamine hydrochloride and sodium acetate to provide ethyl α-hydroxyimino-6-methoxynaphth-2-ylacetate. A solution of 17.55 g of the oxime in 600 ml of methanol containing 5.3 g of zinc metal dust and 135 ml of 50% (v/v) aqueous formic acid was stirred at 0° C. for three hours. After filtering the reaction mixture, the solvent was removed by evaporation to give 10.3 g of ethyl α-amino-α-(6-methoxynaphth-2-yl)acetate.

Workup

  1. filtrationAfter filtering the reaction mixture
  2. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-bb4cce3b74b14bcd93bef3b0ca923585
Source dataset
uspto-grants-1984_12
Patent number
US04490370

Reaction notes

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