5-Aminosalicylic Acid → HCID 12270315, compound

HRID 1579907Notes

Reaction equation

HRID 1579907 reaction equation
[CH2:1]([CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C:11]1=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[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>[C:26]([C:25]1[CH:29]=[C:21]([N:20]2[C:2]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:1][C:10]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[CH2:12][C:11]2=3)[CH:22]=[CH:23][C:24]=1[OH:30])([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 12270345HCID 12270345, compound

Product 1

HCID 12270315HCID 12270315, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.0 g. (0.016 mole) of 1-phenacyl-2-indanone, 2.45 g. (0.016 mole) of 5-aminosalicylic acid and 10 ml. of glacial acetic acid was heated under reflux under nitrogen for 2 hours, cooled and filtered. The collected solid was washed with petroleum ether and recrystallized from acetic acid to provide 4.6 g. (78%) of yellow crystals, m.p. 201°-205°.

Workup

  1. additionA mixture of 4.0 g
  2. temperatureunder reflux under nitrogen for 2 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe collected solid was washed with petroleum ether
  6. customrecrystallized from acetic acid
  7. customto provide 4.6 g

Sources & evidence

ORD record
ord-06c990197ace4257b06abf9516c7cc93
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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