Hydrazine hydrate (1:1) → 2-Naphthohydrazide

HRID 1421915

Reaction equation

HRID 1421915 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)=O)C.O.[NH2:17][NH2:18]>C(O)C>[CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[C:4]([NH:17][NH2:18])=[O:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 76363Ethyl 2-naphthoate

Product 1

HCID 1234852-NaphthohydrazideYield 48.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-naphthyl carboxylic acid ethyl ester (2.0 g, 9.99 mmol) in absolute ethanol (30 ml) was added hydrazine hydrate (4.85 ml, 99.9 mmol) and the reaction mixture was heated at reflux temperature for 72 h. The reaction mixture was cooled and the precipitate was filtered off, washed with 96% ethanol (2×10 ml) and diethyl ether (3×10 ml), dried in vacuo at 50° C. which afforded 0.9 g (48%) of naphthalene-2-carboxylic acid hydrazide as a solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 72 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe precipitate was filtered off
  5. washwashed with 96% ethanol (2×10 ml) and diethyl ether (3×10 ml)
  6. customdried in vacuo at 50° C. which

Sources & evidence

ORD record
ord-8a6b1a4a528e4c76b289a13586b8a40e
Source dataset
uspto-grants-2000_06
Patent number
US06080770

Linked notes

Loading…