4-Chlorobenzaldehyde → HCID 20245839, compound

HRID 1589667Notes

Reaction equation

HRID 1589667 reaction equation
[NH2:1][C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:3]=1.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1>C(O)(=O)C>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[N:1][C:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=3)[N:3]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 125514501-(4-Chlorophenyl)-4,5-dihydro-1H-pyrazol-3-amine

Product 1

HCID 20245839HCID 20245839, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

3-Amino-1-(4-chlorophenyl)-2-pyrazoline (prepared in Reference Example 6 of our European patent specification No. 22-578) (1.95 g) in S.V.M. (5 ml) was mixed with excess 4-chlorobenzaldehyde (1.50 g) and the mixture was heated to reflux after the addition of 1 drop of glacial acetic acid. A virtually clear solution formed which rapidly crystallised to form a bright orange product which was collected, washed with S.V.M. and dried in vacuo to produce 2.95 g 3-(4-chlorobenzylideneamino)-1-(4-chlorophenyl)-2-pyrazoline, m.p. 193°-195° (decomp).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. customA virtually clear solution formed which
  4. customrapidly crystallised
  5. customto form a bright orange product which
  6. customwas collected
  7. washwashed with S.V.M
  8. customand dried in vacuo

Sources & evidence

ORD record
ord-5696915dd23749f28f09b532fceea643
Source dataset
uspto-grants-1986_02
Patent number
US04572913

Reaction notes

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