Salicylaldehyde → HCID 136387293, compound

HRID 1589668Notes

Reaction equation

HRID 1589668 reaction equation
[NH2:1][C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[C:9]([C:14]([F:17])([F:16])[F:15])[CH:8]=2)[N:3]=1.[CH:18](=O)[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[OH:21]>CO.C(O)(=O)C>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([N:4]2[CH2:5][CH2:6][C:2]([N:1]=[CH:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[OH:21])=[N:3]2)=[CH:8][C:9]=1[C:14]([F:17])([F:15])[F:16]

Participants

5

Reactant 2

HCID 6998SalicylaldehydeHCID 202458591-[4-Bromo-3-(trifluoromethyl)phenyl]-4,5-dihydro-1H-pyrazol-3-amine

Product 1

HCID 136387293HCID 136387293, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

3-Amino-1-(4-bromo-3-trifluoromethylphenyl)-2-pyrazoline (prepared in Example 39 of our European patent specification No. 22-578) (140 mg) and salicylaldehyde (100 mg) were dissolved together in methanol (2 ml) and 1 drop of glacial acetic acid. The mixture was heated to reflux for 1 hour. During this time a deep orange-red colour developed and the mixture crystallised. It was kept at 0° for 3 hours, then the solid was collected, washed with methanol and dried in vacuo to yield 150 mg 1-(4-bromo-3-trifluoromethylphenyl)-3-(2-hydroxybenzylideneamino)-2-pyrazoline, m.p. 170° (decomp).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customthe mixture crystallised
  4. customthe solid was collected
  5. washwashed with methanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5b7d2e19012842e89848181ace8d70b4
Source dataset
uspto-grants-1986_02
Patent number
US04572913

Reaction notes

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