STK826163 → HCID 18998824, compound

HRID 1520187Notes

Reaction equation

HRID 1520187 reaction equation
[O:1]1[C:5]2=[CH:6][C:7]3[CH2:8][CH2:9][C:10](=O)[NH:11][C:12]=3[CH:13]=[C:4]2[O:3][CH2:2]1>O1CCCC1>[O:1]1[C:5]2=[CH:6][C:7]3[CH2:8][CH2:9][CH2:10][NH:11][C:12]=3[CH:13]=[C:4]2[O:3][CH2:2]1

Participants

3

Reactant 1

HCID 10583861STK826163

Product 1

HCID 18998824HCID 18998824, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]quinolin-6-one (250 mg, crude) in tetrahydrofuran (50 ml) was dropwise BH3 in THF (1 N, 26 ml). The reaction was stirred at 60° C. overnight. Then the reaction mixture was quenched with hydrogen chloride (3 N), adjusted to pH 8 with sodium bicarbonate, extracted with ethyl acetate (3×50 ml). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford 5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinoline as a solid (180 mg).

Workup

  1. customThen the reaction mixture was quenched with hydrogen chloride (3 N)
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44f1f96a49764ed1a26ffa9c0f90c3ec
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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