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

HRID 1979761Notes

Reaction equation

HRID 1979761 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 was dissolved in 300 ml of acetic acid and under ice-cooled condition with stirring 27 g of sulfuryl chloride dissolved in 100 ml of acetic acid was added dropwise, then the reaction mixture was allowed to stand overnight. The reaction mixture was poured into 1 liter of ice water and the precipitates were obtained by filtration, washed with water, dried and recrystallized from methanol. 30 Grams of 6-chloro-7-methoxy-3,4-dihydrocarbostyril having the melting point of 212° C. was obtained as in the form of colorless needle-like crystals.

Workup

  1. temperaturecooled condition
  2. additionwas added dropwise
  3. customthe precipitates were obtained by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8c907072641e4377a7dc02a4c38b323d
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

Loading…