5-Aminosalicylic Acid → HCID 12270296, compound

HRID 1579900Notes

Reaction equation

HRID 1579900 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[C:5](=O)[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=O.[NH2:19][C:20]1[CH:28]=[C:24]([C:25]([OH:27])=[O:26])[C:23]([OH:29])=[CH:22][CH:21]=1>C(O)(=O)C>[C:25]([C:24]1[CH:28]=[C:20]([N:19]2[C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C:7]=3[CH:6]=[C:5]2[C:4]2[CH:15]=[CH:16][C:17]([Cl:18])=[C:2]([Cl:1])[CH:3]=2)[CH:21]=[CH:22][C:23]=1[OH:29])([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 12270332Cyclohexanone, 2-[2-(3,4-dichlorophenyl)-2-oxoethyl]-

Product 1

HCID 12270296HCID 12270296, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 15 g. (0.05 mole) of 2-(3,4-dichlorophenacyl)cyclohexanone, 7.7 g. (0.05 mole) of 5-aminosalicylic acid, and 63 ml. of glacial acetic acid was heated under reflux under nitrogen for 11/2 hours, cooled and filtered. The collected solid was washed with water and recrystallized from acetonitrile to provide 19.4 g. (97%) of yellow crystals, m.p. 210°-211°.

Workup

  1. temperatureunder reflux under nitrogen for 11/2 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe collected solid was washed with water
  5. customrecrystallized from acetonitrile
  6. customto provide 19.4 g

Sources & evidence

ORD record
ord-c06b016c41054381af21d36717eecdaf
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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