Hydrazine → 4-(Benzyloxy)-3-chlorobenzohydrazide

HRID 1973958Notes

Reaction equation

HRID 1973958 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]([C:13](OCC)=[O:14])=[CH:11][C:10]=1[Cl:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][NH2:22]>CO>[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([NH:21][NH2:22])=[O:14])=[CH:11][C:10]=1[Cl:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 21413907HCID 21413907, compound

Product 1

HCID 124489614-(Benzyloxy)-3-chlorobenzohydrazideYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-benzyloxy-3-chlorobenzoate [c.f., Jones & Robinson, J. Chem. Soc. 3845 (1955)] (32.0 g., 0.11 mole), 25 ml. methanol and 20 ml. 95% hydrazine are stirred under reflux for 8 hours and cooled to room temperature. The mixture is filtered and the resulting solid dried in vacuo to give 29.4 g. 4-benzyloxy- 3-chlorobenzoic acid hydrazide (96.7% yield), m.p. 168°-171° C.

Workup

  1. temperatureunder reflux for 8 hours
  2. filtrationThe mixture is filtered
  3. customthe resulting solid dried in vacuo
  4. customto give 29.4 g

Sources & evidence

ORD record
ord-18ab156da6274b98990f5c5ca8db38a5
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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