5-Aminosalicylic Acid → HCID 12270314, compound

HRID 1579905Notes

Reaction equation

HRID 1579905 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O)[C:8](=O)[CH2:7][CH2:6]2.[NH2:23][C:24]1[CH:32]=[C:28]([C:29]([OH:31])=[O:30])[C:27]([OH:33])=[CH:26][CH:25]=1>C(O)(=O)C>[C:29]([C:28]1[CH:32]=[C:24]([N:23]2[C:8]3[CH2:7][CH2:6][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:10]=4[C:9]=3[CH:13]=[C:14]2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:25]=[CH:26][C:27]=1[OH:33])([OH:31])=[O:30]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 12270343HCID 12270343, compound

Product 1

HCID 12270314HCID 12270314, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5.8 g. (0.02 mole) of 6-methoxy-1-phenacyl-2-tetralone, 3.02 g. (0.02 mole) of 5-aminosalicylic acid, and 20 ml. of glacial acetic acid was heated under reflux for 1 hour, cooled, and filtered. The collected solid was washed with acetic acid and petroleum ether and recrystallized from acetonitrile to provide 5.3 g (67%) of pale yellow crystals, m.p. 233°-234°.

Workup

  1. additionA mixture of 5.8 g
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe collected solid was washed with acetic acid and petroleum ether
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-8d1759f9c96e4a2ca344490662bd0c88
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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