5-Aminosalicylic Acid → HCID 12270294, compound

HRID 1579875Notes

Reaction equation

HRID 1579875 reaction equation
[Br: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>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[N:18]([C:19]3[CH:20]=[CH:21][C:22]([OH:28])=[C:23]([C:24]([OH:26])=[O:25])[CH:27]=3)[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:8]=3[CH:7]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 12270330Cyclohexanone, 2-[2-(4-bromophenyl)-2-oxoethyl]-

Product 1

HCID 12270294HCID 12270294, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 44.3 g. (0.15 mole) of 2-(p-bromophenacyl)cyclohexanone, 23.0 g. (0.15 mole) of 5-aminosalicylic acid, and 115 ml. of glacial acetic acid was heated under reflux for 2 hours, cooled and filtered. The filter cake was washed with water, dried and recrystallized from acetic acid to provide 11.9 g (19%) of tan crystals, m.p. 231°-232°.

Workup

  1. additionA mixture of 44.3 g
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe filter cake was washed with water
  6. customdried
  7. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-cf4ebee0016c477aa80070a94625925c
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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