Hydrazine hydrate (1:1) → 2-Naphthohydrazide

HRID 1741142Notes

Reaction equation

HRID 1741142 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-d30aaf54840242e5be9c7684853fff69
Source dataset
uspto-grants-1999_10
Patent number
US05972978

Reaction notes

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