Aniline → Suberanilic Acid

HRID 2076420Notes

Reaction equation

HRID 2076420 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:8]1[C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:18]>C1COCC1.O>[C:2]1([NH:1][C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([OH:18])=[O:8])=[O:17])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 9543534Oxonane-2,9-dione

Product 1

HCID 9543537Suberanilic AcidYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aniline (0.6 g, 6.4 mmol) was added at room temperature to a stirred solution of oxonane-2,9-dione (1.0 g, 6.4 mmol) in THF anhydrous. After stirring at RT for 0.5 h, the resulting mixture was diluted with water (100 mL). The formed white solid was filtered and collected. Purification by silica gel column chromatography using as eluent EtOAc:cyclohexane=80:20 to 100:0 afforded 7-(phenylcarbamoyl)heptanoic acid as a white solid (174 mg, 11% yield).

Workup

  1. filtrationThe formed white solid was filtered
  2. customcollected
  3. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-f6d85bc389d34e029334cdd535c38686
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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