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 1881254Notes

Reaction equation

HRID 1881254 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-e7e0f99c0c0b45dda98ca2828fe7c2ff
Source dataset
uspto-grants-2012_11
Patent number
US08318784B2

Reaction notes

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