Water → 3-Chloro-6-hydrazino-2-methoxy-5-trifluoromethylpyridine

HRID 1871869Notes

Reaction equation

HRID 1871869 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:8]([Cl:15])=[C:7]([O:16][CH3:17])[N:6]=1.O>C(O)CC>[Cl:15][C:8]1[C:7]([O:16][CH3:17])=[N:6][C:5]([NH:2][NH2:3])=[C:10]([C:11]([F:14])([F:13])[F:12])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 186895102,5-Dichloro-6-methoxy-3-trifluoromethylpyridine

Product 1

HCID 186895243-Chloro-6-hydrazino-2-methoxy-5-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
90 °C

Procedure

10.7 g (0.214 mol) of hydrazine hydrate were added in the course of 10 minutes with stirring at 50° C. to 25.0 g (0.102 mol) of 2,5-dichloro-6-methoxy-3-trifluoromethylpyridine in 100 ml of propanol and the mixture was stirred at 90° C. for 3 hours. After cooling, the resulting suspension was added to 1.2 liters of water, the precipitate was filtered off with suction and taken up in methylene chloride, and the solution was washed with water. The organic phase was dried and concentrated, and the residue was stirred with ether/pentane (1:1). After filtering off with suction and drying, 7.8 g (32% of theory) of the title compound of m.p. 140-142° C. were obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off with suction
  3. washthe solution was washed with water
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. stirringthe residue was stirred with ether/pentane (1:1)
  7. filtrationAfter filtering off with suction
  8. customdrying

Sources & evidence

ORD record
ord-2b6cebd1b92b48a297ebca162bf94059
Source dataset
uspto-grants-2000_08
Patent number
US06107253

Reaction notes

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