Thionyl Chloride → HCID 86679182, compound

HRID 1774830Notes

Reaction equation

HRID 1774830 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14](=[O:20])[CH2:13][CH2:12]3)[CH:6]=[N:7][CH:8]=1.S(Cl)([Cl:23])=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:23][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14](=[O:20])[CH2:13][CH2:12]3)[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86679181HCID 86679181, compound

Product 1

HCID 86679182HCID 86679182, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
3.5 °C

Procedure

At 0° C., 6-(5-hydroxymethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one (190 mg, 0.7 mmol) in DCM (15 mL) was treated slowly with thionyl chloride (0.32 mL, 4.0 mmol). After the addition, the reaction mixture was allowed to stir at 2-5° C. for 2 hours before it was poured into satd. aq. NaHCO3 solution (50 mL). After extraction with EtOAc, the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give title compound (190 mg, 93.5%) as yellow oil. MS: 287.1 (M+H+).

Workup

  1. additionAfter the addition
  2. additionwas poured into satd
  3. extractionAfter extraction with EtOAc
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-994f3bceae744ab88ced6d8571501f12
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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