Hydrochloric Acid → 4-Bromo-5-isoquinolinesulfonyl chloride

HRID 1087495노트

반응식

HRID 1087495 반응식
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([Br:12])=[CH:5][N:6]=[CH:7]2.N([O-])=O.[Na+].[S:17](=[O:19])=[O:18].[ClH:20]>O.C(O)(=O)C>[Br:12][C:4]1[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[S:17]([Cl:20])(=[O:19])=[O:18])[CH:7]=[N:6][CH:5]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 145800574-Bromoisoquinolin-5-amineHCID 23668193Sodium Nitrite

생성물 1

HCID 145800584-Bromo-5-isoquinolinesulfonyl chloride

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

반응 조건

온도
0 °C

실험 절차

4-Bromo-5-isoquinolylsulphonyl chloride may be obtained by the following process: a solution of 5-amino- 4-bromoisoquinoline (4.46 g) in concentrated hydrochloric acid (d=1.19) (44 cc) is cooled to -5° C. then is treated with a solution of sodium nitrite (1.93 g) in water (10 cc). The reaction mixture is stirred for 1 hour at 0° C. The solution obtained is poured into a saturated solution of sulphur dioxide in acetic acid (48 ml), to which has been added a solution of cuprous chloride (0.65 g) in water (5.6 cc). The reaction mixture is stirred until the evolution of gas has finished, and then is extracted with dichloromethane (2×100 cc). The organic phases are pooled, washed with water, dried over magnesium sulphate and concentrated. 4-Bromo-5-isoquino lylsulphonyl chloride (5.6 g) is obtained in the form of a yellow solid which is used as such in the subsequent syntheses.

후처리

  1. customThe solution obtained
  2. stirringThe reaction mixture is stirred until the evolution of gas
  3. extractionis extracted with dichloromethane (2×100 cc)
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a67e11ca1b0d4cc5931d96abf54b54f7
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05036075

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