Water → HCID 178482487, compound

HRID 1284975Notes

Reaction equation

HRID 1284975 reaction equation
[CH:1]([NH:3][C:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:5]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH3:1][NH:3][C:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13306691HCID 13306691, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 178482487HCID 178482487, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3-Formamido-1-(3-trifluoromethylphenyl)-2-pyrazoline (2.4 g) was stirred with dry diethyl ether (60 ml) to produce a slurry which was gradually added to a stirred ice-cold suspension of lithium aluminium hydride (1.0 g) in dry diethyl ether (75 ml) under a nitrogen atmosphere. The addition took place over a period of about 20 minutes and was accompanied by a vigorous reaction. The final reaction mixture was stirred for a further 15 minutes and was then carefully and slowly decomposed by the addition of water (30 ml). The ethereal layer was then decanted off the aqueous sludge which was washed twice with diethyl ether. The combined ethereal solutions were dried over potassium carbonate, filtered and evaporated. The resulting 3-methylamino-1-(3-trifluoromethylphenyl)-2-pyrazoline was a colourless crystalline solid on precipitation by benzene and recrystallization with light petroleum, yield 1.8 g, m.p. 93.1°. The hydrochloride was recrystallized by precipitation from methanol with ether and light petroleum m.p. 206°-207°.

Workup

  1. customto produce a slurry which
  2. additionThe addition
  3. customof about 20 minutes
  4. customwas accompanied by a vigorous reaction
  5. customThe final reaction mixture
  6. customThe ethereal layer was then decanted off the aqueous sludge which
  7. washwas washed twice with diethyl ether
  8. dry with materialThe combined ethereal solutions were dried over potassium carbonate
  9. filtrationfiltered
  10. customevaporated
  11. customon precipitation
  12. customby benzene and recrystallization with light petroleum, yield 1.8 g, m.p. 93.1°
  13. customThe hydrochloride was recrystallized by precipitation from methanol with ether and light petroleum m.p. 206°-207°

Sources & evidence

ORD record
ord-ae22672e5bf8444eb3c56f176f65fdb4
Source dataset
uspto-grants-1986_01
Patent number
US04564684

Reaction notes

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