Hydrazine hydrate (1:1) → 5-Bromo-1-naphthohydrazide

HRID 1276286

Reaction equation

HRID 1276286 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([O:14]C)=O.O.[NH2:17][NH2:18]>CO>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([NH:17][NH2:18])=[O:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 4557673Methyl 5-bromo-1-naphthoate

Product 1

HCID 221158865-Bromo-1-naphthohydrazideYield 65.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-bromo-1-naphthoate (D1) (5.32 g, 20 mmol) and hydrazine hydrate (5.7 ml, 100 mmol) were stirred at reflux in methanol (50 ml) for 48 h. After cooling, the solid was filtered off, washed with cold methanol, and dried in vacuo at 60° C., yielding the title compound (3.48 g, 65%) as a grey-brown crystalline powder.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered off
  3. washwashed with cold methanol
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-df9142386daf43d2804491a3bbe60fda
Source dataset
uspto-grants-2000_12
Patent number
US06166034

Linked notes

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