Oxalyl chloride → 1-Methyl-1,2,3,4-tetrahydroquinoline-6-sulfonyl chloride

HRID 641920Notes

Reaction equation

HRID 641920 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH3:7][N:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([OH:21])(=O)=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1>ClCCl.CN(C=O)C>[CH3:7][N:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([Cl:4])(=[O:21])=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 534141951-Methyl-1,2,3,4-tetrahydroquinoline-6-sulfonic acid

Product 1

HCID 534141961-Methyl-1,2,3,4-tetrahydroquinoline-6-sulfonyl chlorideYield 20.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (20 g, 157.60 mmol) was added dropwise at room temperature to a solution of 1-methyl-1,2,3,4-tetrahydroquinoline-6-sulfonic acid (5 g, 22.00 mmol) in dichloromethane (100 mL) and DMF (10 mL). The resulting solution was stirred for 2 hours, then quenched by adding 200 mL of iced water. The resulting solution was extracted using dichloromethane (2×100 mL), and the combined organics were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using a 1:4 ethyl acetate/petroleum ether solvent system to afford 1.1 g (20.1%) of 1-methyl-1,2,3,4-tetrahydroquinoline-6-sulfonyl chloride as a yellow solid. 1H NMR (CDCl3) δ 7.69 (d, 1H), 7.51 (s, 1H), 6.54 (d, 1H), 3.57 (t, 2H), 3.02 (s, 3H), 2.78 (d, 2H), 1.98 (m, 2H).

Workup

  1. customquenched
  2. additionby adding 200 mL of iced water
  3. extractionThe resulting solution was extracted
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5a679ff602d641e58e1368a96ff8754e
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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