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

HRID 231035

Reaction equation

HRID 231035 reaction equation
[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

Participants

5

Reactant 3

HCID 180Acetone3×HCID 14264Propane sultone2×HCID 47150296-Bromo-1,2,3,4-tetrahydroquinoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-22d7a5074a3a4ebaaab61baf7d5c1fee
Source dataset
uspto-grants-1989_07
Patent number
US04845030

Linked notes

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