Sulfuryl chloride → 6-Chloro-7-methoxy-3,4-dihydrocarbostyril

HRID 569947Notes

Reaction equation

HRID 569947 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.S(Cl)([Cl:17])(=O)=O>C(O)(=O)C>[Cl:17][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[NH:10][C:9](=[O:13])[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 128994187-Methoxy-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 128994196-Chloro-7-methoxy-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

35.4 Grams of 7-methoxy-3,4-dihydrocarbostyril are dissolved in 300 ml of acetic acid. This solution is stirred under ice-cooling conditions, and 100 ml of acetic acid solution containing 27 g of sulfuryl chloride are added dropwise and allowed to stand overnight. The reaction mixture is poured into 1 liter of ice-water and the precipitate thus formed is separated by filtration, washed with water and dried. Recrystallization from methanol obtains 30 g of 6-chloro-7-methoxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with a melting point of 212° C.

Workup

  1. additionare added dropwise
  2. customthe precipitate thus formed
  3. customis separated by filtration
  4. washwashed with water
  5. customdried
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-85cd80c1283d470383c4a24d532a17e4
Source dataset
uspto-grants-1988_03
Patent number
US04734416

Reaction notes

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