Propane sultone → 3-(5-Hydroxy-3,4-dihydro-2h-quinoline-1-yl)propanesulfonic acid

HRID 1923443

Reaction equation

HRID 1923443 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][NH:7]2.[CH2:12]1[CH2:18][S:15](=[O:17])(=[O:16])[O:14][CH2:13]1>C(#N)CCC>[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[CH2:13][CH2:12][CH2:18][S:15]([OH:17])(=[O:16])=[O:14]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 30460361,2,3,4-Tetrahydroquinolin-5-ol

Product 1

HCID 591417083-(5-Hydroxy-3,4-dihydro-2h-quinoline-1-yl)propanesulfonic acid

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 0.8 g (5.36 mmol) of 5-hydroxy-1,2,3,4-tetrahydroquinoline and 0.5 g 1,3-propanesultone (4.1 mmol) in 12 ml of butyronitrile was heated at 125° C. for hours. The mixture was suction filtered and the filtrate evaporated under reduced pressure. The resulting off white compound crystallized. Product washed with ethyl ether and filtered of. Yield 0.8 g (80%)

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated under reduced pressure
  3. customThe resulting off white compound crystallized
  4. washProduct washed with ethyl ether
  5. filtrationfiltered of

Sources & evidence

ORD record
ord-4f75fb939d874ca8b65e784e6f4dfb10
Source dataset
uspto-grants-2012_05
Patent number
US08178360B2

Linked notes

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