5-Aminosalicylic Acid → HCID 21569613, compound

HRID 1579902Notes

Reaction equation

HRID 1579902 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([C:6](=O)[CH2:7][CH:8]2[CH2:12][CH2:11][CH2:10][C:9]2=O)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:26]=[C:22]([C:23]([OH:25])=[O:24])[C:21]([OH:27])=[CH:20][CH:19]=1>C(O)(=O)C>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]2[N:17]([C:18]3[CH:19]=[CH:20][C:21]([OH:27])=[C:22]([C:23]([OH:25])=[O:24])[CH:26]=3)[C:9]3[CH2:10][CH2:11][CH2:12][C:8]=3[CH:7]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 21569627HCID 21569627, compound

Product 1

HCID 21569613HCID 21569613, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 20.8 g. (0.07 mole) of 2-(p-bromophenacyl)cyclopentanone, 10.71 g. (0.07 mole) of 5-aminosalicylic acid, and 88 ml. of glacial acetic acid was heated under reflux under nitrogen for 31/2 hours, cooled and filtered. The collected solid was chromatographed on silica gel. The solid eluted with benzene was recrystallized from ethanol-water to provide tan crystals, m.p. 215°-216°.

Workup

  1. temperatureunder reflux under nitrogen for 31/2 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe collected solid was chromatographed on silica gel
  5. washThe solid eluted with benzene
  6. customwas recrystallized from ethanol-water
  7. customto provide tan crystals, m.p. 215°-216°

Sources & evidence

ORD record
ord-e5df2f1c4616447f8d6f287fd4936098
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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