Propane sultone → 1,2,3,4-Tetrahydroquinoline-N-propanesulphonic acid

HRID 231034

Reaction equation

HRID 231034 reaction equation
[CH2:1]1[S:5](=[O:7])(=[O:6])[O:4][CH2:3][CH2:2]1.[NH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1>CO>[N:8]1([CH2:3][CH2:2][CH2:1][S:5]([OH:4])(=[O:7])=[O:6])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 92497391,2,3,4-Tetrahydroquinoline-N-propanesulphonic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

48.8 molten propane-1,3-sultone were added dropwise at 60+ to 80° C. within the course of 50 minutes to 58.4 g 1,2,3,4-tetrahydroquinoline in a 500 ml. flask. The reaction mixture was left for 3.45 hours at about 70° C. and subsequently 470 ml. methanol were added portionwise under reflux conditions and further stirred under reflux conditions until the solid, glasslike under material had dissolved completely. Thereafter, the reaction mixture was cooled to ambient temperature, while stirring, a rapid crystallization thereby taking place. After leaving to stand for about 12 hours in a refrigerator, the crystals were filtered off. Yield about 50 g.; m.p. 233°-237° C.

Workup

  1. dissolutionhad dissolved completely
  2. stirringwhile stirring
  3. customa rapid crystallization
  4. customAfter leaving
  5. waitto stand for about 12 hours in a refrigerator
  6. filtrationthe crystals were filtered off

Sources & evidence

ORD record
ord-a5d6c7e92cdf434286cb8502d02db8d3
Source dataset
uspto-grants-1989_07
Patent number
US04845030

Linked notes

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