Acetone → 6-Bromo-1,2,3,4-tetrahydroquinoline-N-propanesulphonic acid

HRID 231035

반응식

HRID 231035 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.CC(C)=O.[CH2:16]1[S:20](=[O:22])(=[O:21])[O:19][CH2:18][CH2:17]1>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:18][CH2:17][CH2:16][S:20]([OH:22])(=[O:21])=[O:19])[CH2:7][CH2:6][CH2:5]2

참가 물질

5

반응물 3

HCID 180Acetone3회HCID 14264Propane sultone2회HCID 47150296-Bromo-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 200343806-Bromo-1,2,3,4-tetrahydroquinoline-N-propanesulphonic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

4.2 g of the 6-bromo-1,2,3,4-tetra-hydroquinoline obtained according to a) above were dissolved in 0 ml. acetone and, while stirring at 50° C., 2.44 g. molten propane-1,3-sultone, dissolved in 20 ml. acetone, were added dropwise within the course of 30 minutes. After boiling under reflux for 24 hours, a further 2.44 g. molten propanesultone, dissolved in 20 ml. acetone, were added dropwise under the same conditions. After boiling under reflux for 48 hours, the reaction mixture was subjected to column chromatography (silica gel; elution agent chloroform/methanol=1/1 v/v; 25 ml. fractions); fractions 6-10 were evaporated in a vacuum at 35° C., the 1.8 g. of red-brown residue obtained was stirred with about 20 ml. methanol and 1.05 g of sand-coloured crystals were obtained; m.p. 217° C. (decomp.).

후처리

  1. dissolutionabove were dissolved in 0 ml
  2. temperatureunder reflux for 24 hours
  3. temperatureunder reflux for 48 hours
  4. washthe reaction mixture was subjected to column chromatography (silica gel; elution agent chloroform/methanol=1/1 v/v; 25 ml. fractions)
  5. customfractions 6-10 were evaporated in a vacuum at 35° C.
  6. customof red-brown residue obtained

출처 및 근거

ORD 기록
ord-22d7a5074a3a4ebaaab61baf7d5c1fee
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845030

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