5-Aminosalicylic Acid → HCID 12270309, compound

HRID 1579898Notes

Reaction equation

HRID 1579898 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][C:6](=O)[CH:5]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)[CH2:4]1.[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:6]3[CH2:7][CH2:8][CH:3]([O:2][CH3:1])[CH2:4][C:5]=3[CH:10]=[C:11]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:21]=[CH:22][C:23]=1[OH:29])([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 21491546HCID 21491546, compound

Product 1

HCID 12270309HCID 12270309, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 24.6 g. (0.1 mole) of 4-methoxy-2-phenacylcyclohexanone, 15.3 g. (0.1 mole) of 5-aminosalicylic acid, and 80 ml. of glacial acetic acid was heated under reflux for 1.5 hours, filtered, cooled and again filtered. The collected solid was washed with acetic acid and petroleum ether and recrystallized from acetonitrile to provide 22.5 g. (62%) of crystals, m.p. 207°-210°.

Workup

  1. additionA mixture of 24.6 g
  2. temperatureunder reflux for 1.5 hours
  3. filtrationfiltered
  4. temperaturecooled
  5. filtrationagain filtered
  6. washThe collected solid was washed with acetic acid and petroleum ether
  7. customrecrystallized from acetonitrile
  8. customto provide 22.5 g

Sources & evidence

ORD record
ord-b3d7a796df3649cb928777d715ff027d
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

Loading…