4-Aminosalicylic Acid → HCID 12270274, compound

HRID 1579861Notes

Reaction equation

HRID 1579861 reaction equation
[CH2:1]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[NH2:17][C:18]1[CH:19]=[C:20]([OH:27])[C:21](=[CH:25][CH:26]=1)[C:22]([OH:24])=[O:23]>C(O)(=O)C>[C:22]([C:21]1[CH:25]=[CH:26][C:18]([N:17]2[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=3[CH:1]=[C:2]2[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:19][C:20]=1[OH:27])([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 46494-Aminosalicylic AcidHCID 105128992-(2-Oxo-2-phenylethyl)cyclohexanone

Product 1

HCID 12270274HCID 12270274, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 32.4 g. (0.15 mole) of 2-phenacylcyclohexanone, 23.0 g. (0.15 mole) of 4-aminosalicylic acid and 90 ml. of glacial acetic acid was heated under reflux for 7 hours, cooled, diluted with 90 ml. of water and extracted with ether. The ether solution was dried over sodium sulfate and concentrated. The residue was recrystallized from benzene-ethanol to provide 3.36 g. (7%) of yellow crystals, m.p. 193°-195°.

Workup

  1. temperatureunder reflux for 7 hours
  2. temperaturecooled
  3. additiondiluted with 90 ml
  4. extractionof water and extracted with ether
  5. dry with materialThe ether solution was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from benzene-ethanol
  8. customto provide 3.36 g

Sources & evidence

ORD record
ord-4c6d588b6ff34bcd90462c14938fcc72
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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