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

HRID 1458244Notes

Reaction equation

HRID 1458244 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 at 50° C. in the course of 10 minutes with stirring 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 for 3 hours at 90° C. After cooling, the resulting suspension was poured into 1.2 liters of water, and the precipitate was filtered off with suction, taken up in methylene chloride and washed with water. The organic phase was dried and concentrated, and the residue was stirred with ether/pentane (1:1). After filtration with suction and drying, 7.8 g (32% of theory) of the title compound of m.p. 140°-142° C. (Table II, No. 2.011) were obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off with suction
  3. washwashed with water
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. stirringthe residue was stirred with ether/pentane (1:1)
  7. filtrationAfter filtration with suction
  8. customdrying
  9. custom2.011) were obtained

Sources & evidence

ORD record
ord-0b68efed61b44267a8e22e9af6e7d949
Source dataset
uspto-grants-1998_12
Patent number
US05849920

Reaction notes

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