Dichloromethane → 1-Methyl-1,2,3,4-tetrahydroquinoline-7-sulfonyl chloride

HRID 641917

Reaction equation

HRID 641917 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[SH:12]([O:15]Cl)(=O)=[O:13].[Cl:17]CCl>>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12]([Cl:17])(=[O:15])=[O:13])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 681091,2,3,4-Tetrahydro-1-methylquinolineHCID 178527254HCID 178527254, compound

Product 1

HCID 534141971-Methyl-1,2,3,4-tetrahydroquinoline-7-sulfonyl chlorideYield 8%

Procedure

A solution of 1-methyl-1,2,3,4-tetrahydroquinoline (10 g, 68.03 mmol) in dichloromethane (20 mL) was added dropwise to HSO3Cl (80 g, 689.66 mmol) at 0-5° C., and the resulting solution was maintained at room temperature overnight. The reaction mixture was then quenched by adding 300 mL of iced water. The resulting solution was extracted using ethyl acetate (3×150 mL). The organic layers were combined, concentrated, and the residue was purified by column chromatography using a 1:20 ethyl acetate/petroleum ether solvent system to afford 1-methyl-1,2,3,4-tetrahydroquinoline-7-sulfonyl chloride as a yellow liquid in 8% yield. 1H NMR (CDCl3) δ 7.19 (d, 1H), 7.10 (d, 1H), 7.06 (s, 1H), 3.33 (t, 2H), 2.97 (s, 3H), 2.81 (d, 2H), 1.99 (m, 2H).

Workup

  1. customThe reaction mixture was then quenched
  2. additionby adding 300 mL of iced water
  3. extractionThe resulting solution was extracted
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0b5a9f789336410781473493566b8633
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Linked notes

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