Hydrazine hydrate (1:1) → Methyl 6-chloro-4-hydrazinonicotinate

HRID 1833336Notes

Reaction equation

HRID 1833336 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[C:9]([O:11][CH3:12])=[O:10].O.[NH2:14][NH2:15]>CO>[Cl:8][C:6]1[N:5]=[CH:4][C:3]([C:9]([O:11][CH3:12])=[O:10])=[C:2]([NH:14][NH2:15])[CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2764083Methyl4,6-dichloronicotinate

Product 1

HCID 45588417Methyl 6-chloro-4-hydrazinonicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

205 g. of 4,6-dichloro-3-pyridinecarboxylic acid, methyl ester (1 mol.) are dissolved in 1 liter of methanol. The solution is cooled to 0° and 100 g. of hydrazine hydrate are dropped in with stirring. The solution is kept at 0° for 12 hours. The precipitated 6-chloro-4-hydrazino-3-pyridinecarboxylic acid, methyl ester is filtered off and recrystallized from methanol, yield: 175 g. (87%); m.p. 163.3°.

Workup

  1. temperatureThe solution is cooled to 0°
  2. filtrationThe precipitated 6-chloro-4-hydrazino-3-pyridinecarboxylic acid, methyl ester is filtered off
  3. customrecrystallized from methanol, yield: 175 g

Sources & evidence

ORD record
ord-ee657abe7bd54ca5b5446ce188eb7b37
Source dataset
uspto-grants-1978_01
Patent number
US04066645

Reaction notes

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