5-Aminosalicylic Acid → HCID 12270293, compound

HRID 1579886Notes

Reaction equation

HRID 1579886 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6](=O)[CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=O)=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:27]=[C:23]([C:24]([OH:26])=[O:25])[C:22]([OH:28])=[CH:21][CH:20]=1>C(O)(=O)C>[C:24]([C:23]1[CH:27]=[C:19]([N:18]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][C:2]([F:1])=[CH:3][CH:4]=2)[CH:20]=[CH:21][C:22]=1[OH:28])([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 12270329Cyclohexanone, 2-[2-(4-fluorophenyl)-2-oxoethyl]-

Product 1

HCID 12270293HCID 12270293, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 17.9 g. (0.077 mole) of 2-(p-fluorophenacyl)cyclohexanone, 11.8 g. (0.077 mole) of 5-aminosalicylic acid, and 90 ml. of glacial acetic acid was heated under reflux under nitrogen for 43/4 hours, cooled and filtered. The collected solid was washed with water and recrystallized from acetic acid to provide 10.0 g. (37%) of yellow crystals, m.p. 239°-240°.

Workup

  1. temperatureunder reflux under nitrogen for 43/4 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe collected solid was washed with water
  5. customrecrystallized from acetic acid
  6. customto provide 10.0 g

Sources & evidence

ORD record
ord-13a3dc3679ce42ecb3e39e9ed115e36e
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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