Hydrazine hydrate (1:1) → HCID 14951339, compound

HRID 973954Notes

Reaction equation

HRID 973954 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=1[NH:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16](OC)=[O:17]>CO>[Cl:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=1[NH:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([NH:2][NH2:3])=[O:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 76743Benzoic acid, 2-((2,6-dichloro-3-methylphenyl)amino)-, methyl ester

Product 1

HCID 14951339HCID 14951339, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Hydrazine hydrate (2 ml) is added dropwise to a suspension of methyl 2-[(2,6-dichloro-3-methylphenyl)amino]-benzoate (227.1 mg, .73 mmol) in 10 ml of methanol. The reaction mixture is heated at 60° C for seven hours under an atmosphere of nitrogen and then allowed to cool to room temperature overnight. The now clear colorless solution is concentrated in vacuo and chromatographed, eluting with ethyl acetate and hexane (gradient of 1:2 to 1:1), providing 208.6 mg (92%) of a white solid, mp 158°-160° C.

Workup

  1. temperatureto cool to room temperature overnight
  2. concentrationThe now clear colorless solution is concentrated in vacuo
  3. customchromatographed
  4. washeluting with ethyl acetate and hexane (gradient of 1:2 to 1:1)

Sources & evidence

ORD record
ord-f23f884631cb4b71b456d367c6232979
Source dataset
uspto-grants-1991_11
Patent number
US05066668

Reaction notes

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