5-Aminosalicylic Acid → HCID 12270297, compound

HRID 1579892Notes

Reaction equation

HRID 1579892 reaction equation
[OH: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]([OH: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 12270333Cyclohexanone, 2-[2-(4-hydroxyphenyl)-2-oxoethyl]-

Product 1

HCID 12270297HCID 12270297, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 11.5 g. (0.05 mole) of 2-(p-hydroxyphenacyl)cyclohexanone, 7.6 g. (0.05 mole) of 5-aminosalicylic acid, and 40 ml. of glacial acetic acid was heated under reflux under nitrogen for 1.5 hours, cooled and filtered to provide 10.6 g. (61%) of solid, m.p. 214°-217°. Recrystallization from acetonitrile gave crystals, m.p. 217°-219°.

Workup

  1. additionA mixture of 11.5 g
  2. temperatureunder reflux under nitrogen for 1.5 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customto provide 10.6 g
  6. customRecrystallization from acetonitrile
  7. customgave crystals, m.p. 217°-219°

Sources & evidence

ORD record
ord-73567ef441ca489ca586a551a5cd9df0
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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