HCID 318223, compound → HCID 2729275, compound

HRID 616426Notes

Reaction equation

HRID 616426 reaction equation
[C:1]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O)(=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C]=O>[Pd].C(#N)C>[CH:2]([C:1]1[O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]=1)=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 318223HCID 318223, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 2729275HCID 2729275, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
190 °C

Procedure

An autoclave is charged with 13.45 g. o-nitrophenyl cinnamate, 2.5 g. 5% palladium-on-carbon, 0.40 g. ferric chloride and 90 ml. anhydrous acetonitrile, pressurized with carbon monoxide to 5000 psig., and heated at 190° C. for 6 hours. After the catalyst is removed by filtration, analysis of the reaction mixture by vapor phase chromatography shows that 2-styrylbenzoxazole is the major product. The 2-styrylbenzoxazole is isolated by chromatography on alumina using benzene as the eluent. After recrystallization from petroleum ether, it melts at 78°-79° C. and is identical with an authentic sample of 2-styrylbenzoxazole by mixed melting point, infrared spectrum and vapor phase chromatography.

Workup

  1. additionAn autoclave is charged with 13.45 g
  2. customAfter the catalyst is removed by filtration, analysis of the reaction mixture by vapor phase chromatography

Sources & evidence

ORD record
ord-528ab0ddfbbd4c3aa2e095b98da904b0
Source dataset
uspto-grants-1978_02
Patent number
US04074046

Reaction notes

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