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

HRID 1290145Notes

Reaction equation

HRID 1290145 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-68635ec9ab6242889ee81ec42ce39154
Source dataset
uspto-grants-1998_05
Patent number
US05750705

Reaction notes

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