5-Aminosalicylic Acid → HCID 12270312, compound

HRID 1579860Notes

Reaction equation

HRID 1579860 reaction equation
[CH2:1]([CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[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[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[CH2:18][CH2:19][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 122703462-phenacyl-1-tetralone

Product 1

HCID 12270312HCID 12270312, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 20.0 g. (0.076 mole) of 2-phenacyl-1-tetralone, 11.6 g. (0.076 mole) of 5-aminosalicylic acid, and 70 ml. of glacial acetic acid was heated under reflux for 4 hours, cooled diluted with 10 ml. of water and filtered. The filter cake was washed with water and dried to provide 15.5 g. of solid, m.p. 215°-218°. Recrystallization from benzene-cyclohexane gave 6.5 g. (22%) of yellow crystals, m.p. 245°-247°.

Workup

  1. additionA mixture of 20.0 g
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. additiondiluted with 10 ml
  5. filtrationof water and filtered
  6. washThe filter cake was washed with water
  7. customdried
  8. customto provide 15.5 g
  9. customRecrystallization from benzene-cyclohexane
  10. customgave 6.5 g

Sources & evidence

ORD record
ord-c11844c4de10490c93356c783e4fe7c5
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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