Sodium Bicarbonate → STK826163

HRID 1520186Notes

Reaction equation

HRID 1520186 reaction equation
[N+:1]([C:4]1[C:5](/[CH:13]=[CH:14]/[C:15]([O:17]CC)=O)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)([O-])=O.C([O-])(O)=O.[Na+]>[Pd].CC(O)=O>[O:11]1[C:7]2=[CH:6][C:5]3[CH2:13][CH2:14][C:15](=[O:17])[NH:1][C:4]=3[CH:12]=[C:8]2[O:9][CH2:10]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 13317300HCID 13317300, compound

Product 1

HCID 10583861STK826163

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Palladium on carbon (340 mg) was added to a solution of (E)-ethyl 3-(6-nitrobenzo[d][1,3]dioxol-5-yl)acrylate (500 mg, 1.89 mmol) in AcOH (60 ml). Then H2 (g) was introduced at 5 Atm and the reaction was stirred overnight at 70° C. The reaction mixture was adjusted to pH 8 with saturated aqueous NaHCO3 and extracted with ethyl acetate (3×80 ml). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford 2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]quinolin-6-one as a brown solid (316 mg, crude).

Workup

  1. additionThen H2 (g) was introduced at 5 Atm
  2. extractionextracted with ethyl acetate (3×80 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f8a7540290a423cb9cd90ad35362cea
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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