Phosphorus oxychloride → 4-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile

HRID 612032노트

반응식

HRID 612032 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](O)=[C:11]([C:16]#[N:17])[CH:12]=[N:13]2)=[CH:8][C:7]=1[O:19][CH3:20].P(Cl)(Cl)([Cl:23])=O>>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([Cl:23])=[C:11]([C:16]#[N:17])[CH:12]=[N:13]2)=[CH:8][C:7]=1[O:19][CH3:20]

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 1784867617-(3-Chloropropoxy)-4-hydroxy-6-methoxyquinoline-3-carbonitrile

생성물 1

HCID 112206374-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile

실험 절차

A mixture of 3.5 g (12 mmol) of 7-(3-chloro-propoxy)-4-hydroxy-6-methoxy-quinoline-3-carbonitrile and 28 ml of phosphorous oxychloride was refluxed for 1.5 hr. Excess reagent was removed at reduced pressure. The residue was mixed with ice cold dilute sodium hydroxide and ethyl acetate. The mixture was extracted with a combination of ethyl acetate and tetrahydrofuran. The combined extracts were washed with a saturated solution of sodium bicarbonate, dried over magnesium sulfate, and filter through a short column of silica gel. Solvents were removed giving 3.2 g of the title compound as a pink solid that is used with additional purification.

후처리

  1. temperaturewas refluxed for 1.5 hr
  2. customExcess reagent was removed at reduced pressure
  3. additionThe residue was mixed with ice cold dilute sodium hydroxide and ethyl acetate
  4. extractionThe mixture was extracted with a combination of ethyl acetate and tetrahydrofuran
  5. washThe combined extracts were washed with a saturated solution of sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfilter through a short column of silica gel
  8. customSolvents were removed

출처 및 근거

ORD 기록
ord-04f9f9ff87c04400b72ae4d3d556bb0b
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06002008

반응 노트

불러오는 중…