Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one

HRID 883191Notes

Reaction equation

HRID 883191 reaction equation
O[C:2]1[C:10]([NH:11][C:12](=[O:14])[CH3:13])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:15])[CH2:5][CH2:6]2.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[CH3:13][C:12]1[O:14][C:2]2[C:3]3[C:4](=[O:15])[CH2:5][CH2:6][C:7]=3[CH:8]=[CH:9][C:10]=2[N:11]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67354064N-(4-Hydroxy-3-oxo-2,3-dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 577812772-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-oneYield 85%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

N-(4-Hydroxy-3-oxo-2,3-dihydro-1H-inden-5-yl)acetamide (469 mg, 2.29 mmol) and pyridinium p-toluenesulfonate (115 mg, 0.457 mmol) were heated under reflux in xylene (23 mL) for 2.5 hr. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→100/0) to give the title compound (363 mg, yield 85%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→100/0)

Sources & evidence

ORD record
ord-577eb0cf8bef46c7b2c4fe2f74310e32
Source dataset
uspto-grants-2012_08
Patent number
US08236837B2

Reaction notes

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