Benzenesulfonyl chloride → HCID 59778167, compound

HRID 1643894Notes

Reaction equation

HRID 1643894 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].CCN(C(C)C)C(C)C.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC#N>[O:12]=[C:3]1[CH:2]([NH:1][S:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:30])=[O:29])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 134994273-Amino-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 59778167HCID 59778167, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-amino-3,4-dihydro-1H-quinolin-2-one (177.6 mg, 0.59 mmol) (prepared according to the procedures by Davis, A. L.; et al, Arch. Biochem. Biophys., 102, 48 (1963)) in CH3CN (5 mL) was added DIPEA (0.24 mL, 1.44 mmol), followed by addition of benzene sulfonylchloride (0.09 mL, 0.71 mmol). The mixture was stirred at RT for 1.5 h, then concentrated in vacuo. The residue was taken into EtOAc (30 mL), washed with water, brine, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc (50-90%) in hexane to give the title compound (140 mg, 78%).

Workup

  1. customprepared
  2. concentrationconcentrated in vacuo
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed (silica gel)
  7. washeluting with EtOAc (50-90%) in hexane

Sources & evidence

ORD record
ord-30465f2f2073474caeec16eb0f729e1f
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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