5-Aminosalicylic Acid → HCID 12270298, compound

HRID 1579871Notes

Reaction equation

HRID 1579871 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[C:6](=O)[CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O.[NH2:21][C:22]1[CH:30]=[C:26]([C:27]([OH:29])=[O:28])[C:25]([OH:31])=[CH:24][CH:23]=1>C(O)(=O)C>[C:27]([C:26]1[CH:30]=[C:22]([N:21]2[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:8]=3[CH:7]=[C:6]2[C:5]2[CH:16]=[CH:17][CH:18]=[C:3]([C:2]([F:20])([F:19])[F:1])[CH:4]=2)[CH:23]=[CH:24][C:25]=1[OH:31])([OH:29])=[O:28]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 12270334Cyclohexanone, 2-[2-oxo-2-[3-(trifluoromethyl)phenyl]ethyl]-

Product 1

HCID 12270298HCID 12270298, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 12.0 g. (0.042 mole) of 2-(m-trifluoromethylphenacyl)cyclohexanone, 6.45 g. (0.042 mole) of 5-aminosalicylic acid, and 30 ml. of glacial acetic acid was heated under reflux for 4 hours and filtered. The filtrate was diluted with water and the supernatant was decanted from the oil which separated. Trituration with cyclohexane gave 7.7 g. of solid, m.p. 215°-225°. Recrystallization from isopropyl alcohol-water afforded 4.1 g. (47%) of crystals, m.p. 223°-225°.

Workup

  1. additionA mixture of 12.0 g
  2. temperatureunder reflux for 4 hours
  3. filtrationfiltered
  4. additionThe filtrate was diluted with water
  5. customthe supernatant was decanted from the oil which
  6. customseparated
  7. customTrituration with cyclohexane gave 7.7 g
  8. customRecrystallization from isopropyl alcohol-water
  9. customafforded 4.1 g

Sources & evidence

ORD record
ord-42f41fc3bfba4ed69c96ec8d12ac8427
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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