Ethyl Acetate → HCID 2308242, compound

HRID 1589664Notes

Reaction equation

HRID 1589664 reaction equation
[NH2:1][C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[N:3]=1.C(O[CH2:21][CH3:22])(=O)C>CO.C(O)C>[N:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:21]=1[CH:22]=[N:1][C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 477954,5-Dihydro-1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amine

Product 1

HCID 2308242HCID 2308242, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

3-Amino-1-(3-trifluoromethylphenyl)-2-pyrazoline in methanol (23 ml) was stirred together with 2-pyridylaldehyde at room temperature for 2 hours and then under reflux for a further 2 hours. Thin layer chromatography (SiO2, ethyl acetate) indicated that the reaction was substantially complete. After standing overnight, additional 2-pyridylaldehyde (0.5 g) was added and heating was continued for 2 hours. TLC again indicated that no further reaction had occurred. The reaction mixture was evaporated in vacuo to yield an orange-coloured solid which was stirred for 45 minutes in aqueous ethanol (3:1) and 3-(2-pyridylmethyleneamino)-1-(3-trifluoromethylphenyl)-2-pyrazoline was collected, m.p. 155.6°.

Workup

  1. temperatureunder reflux for a further 2 hours
  2. temperatureheating
  3. waitwas continued for 2 hours
  4. customTLC again indicated that no further reaction
  5. customThe reaction mixture was evaporated in vacuo
  6. customto yield an orange-coloured solid which
  7. custom3-(2-pyridylmethyleneamino)-1-(3-trifluoromethylphenyl)-2-pyrazoline was collected

Sources & evidence

ORD record
ord-95e7e8c0bcbc4c25ac522e46877717bd
Source dataset
uspto-grants-1986_02
Patent number
US04572913

Reaction notes

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