Acetic Acid → HCID 12270300, compound

HRID 1579904Notes

Reaction equation

HRID 1579904 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8](=O)[CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:20][C:21]1[CH:29]=[C:25]([C:26]([OH:28])=[O:27])[C:24]([OH:30])=[CH:23][CH:22]=1.C(O)(=O)C>O>[C:26]([C:25]1[CH:29]=[C:21]([N:20]2[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=3[CH:9]=[C:8]2[C:7]2[CH:18]=[CH:19][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:22]=[CH:23][C:24]=1[OH:30])([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 40755-Aminosalicylic AcidHCID 12270335HCID 12270335, compound

Product 1

HCID 12270300HCID 12270300, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 40 g. (0.15 mole) of 2-(p-nitrophenacyl)cyclohexanone, 23 g. (0.15 mole) of 5-aminosalicylic acid and 187 ml. of glacial acetic acid was heated under reflux under nitrogen for 3 3/4 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate solution was dried over sodium sulfate and concentrated to a red solid which was chromatographed on silica gel. The material eluted with 3% methanol in chloroform was recrystallied from acetonitrile to provide 3.8 g. (7%) of orange crystals, m.p. 241°-242°.

Workup

  1. additionA mixture of 40 g
  2. temperatureunder reflux under nitrogen for 3 3/4 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  5. concentrationconcentrated to a red solid which
  6. customwas chromatographed on silica gel
  7. washThe material eluted with 3% methanol in chloroform
  8. customto provide 3.8 g

Sources & evidence

ORD record
ord-16fcb239871a4cecb1b10419b2f3ac75
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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