5-Aminosalicylic Acid → Fendosal

HRID 1579878Notes

Reaction equation

HRID 1579878 reaction equation
[CH2:1]([CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[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.[NH2:21][C:22]1[CH:30]=[C:26]([C:27]([OH:29])=[O:28])[C:25]([OH:31])=[CH:24][CH:23]=1>C(O)(=O)C>[C:27]([C:26]1[CH:30]=[C:22]([N:21]2[C:11]3[CH2:12][CH2:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]=3[CH:1]=[C:2]2[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:23]=[CH:24][C:25]=1[OH:31])([OH:29])=[O:28]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 122703441-(2-Oxo-2-phenyl-ethyl)-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 40821Fendosal

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 16.6 g. (0.063 mole) of 1-phenacyl-2-tetralone, 9.65 g. (0.063 mole) of 5-aminosalicylic acid, and 60 ml. of glacial acetic acid was heated under reflux under nitrogen for 2 hours, cooled and filtered. The collected solid was washed with acetic acid and water, dried and recrystallized from acetic acid to provide 16.3 g. (68%) of crystals, m.p. 223°-225°.

Workup

  1. additionA mixture of 16.6 g
  2. temperatureunder reflux under nitrogen for 2 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe collected solid was washed with acetic acid and water
  6. customdried
  7. customrecrystallized from acetic acid
  8. customto provide 16.3 g

Sources & evidence

ORD record
ord-9124a46e6a85416ba27ab81c85da581e
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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