3,4-Methylenedioxy-6-nitrocinnamic acid → STK826163

HRID 2260642Notes

Reaction equation

HRID 2260642 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([CH:10]=[CH:11][C:12](O)=[O:13])[CH:7]=2)[O:2]1>CN(C=O)C.C(O)C.Cl.[Pd]>[CH2:1]1[O:2][C:3]2[CH:4]=[C:5]3[C:6]([CH2:10][CH2:11][C:12](=[O:13])[NH:15]3)=[CH:7][C:8]=2[O:9]1

Participants

6

Reactant 1

HCID 2282673,4-Methylenedioxy-6-nitrocinnamic acid

Product 1

HCID 10583861STK826163Yield 80.9%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

3-(4,5-methylenedioxy-2-nitrophenyl)acrylic acid (10 g, 42 mmol) in 50 ml dry DMF, 450 ml absolute ethanol and 1.5 ml conc. HCl was reduced catalytically at 1 atm., 22° C., using 1.5 g 5% palladium on carbon to give 6.5 g 6,7-methylenedioxy-1,2,3,4-tetrahydro-2-oxoquinoline as light brown crystals, which was used without further purification.

Workup

  1. customwas reduced catalytically at 1 atm., 22° C.

Sources & evidence

ORD record
ord-65451a9669dc43a58c7df122d93a7db6
Source dataset
uspto-grants-1995_12
Patent number
US05478845

Reaction notes

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