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

HRID 1088289Notes

Reaction equation

HRID 1088289 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, 0.73 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-8050e084aa914edc8bcfa525df98c37f
Source dataset
uspto-grants-1990_10
Patent number
US04962119

Reaction notes

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