6-Methoxy-m-toluenesulfonyl chloride → 1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid methyl ester

HRID 1715844Notes

Reaction equation

HRID 1715844 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11][NH:12]2)=[CH:7][CH:6]=1)=[O:4].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[S:24](Cl)(=[O:26])=[O:25]>ClCCl.N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11][N:12]2[S:24]([C:18]2[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=2[O:16][CH3:15])(=[O:26])=[O:25])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 1451496-Methoxy-m-toluenesulfonyl chlorideHCID 16244389Methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate

Product 1

HCID 684326051-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1,2,3,4-tetrahydro-quinoline-7-carboxylic acid methyl ester (23.00 g, 0.12 mol) in dichloromethane (0.70 L) and pyridine (0.10 L) was treated with 2-methoxy-5-methyl-benzenesulfonyl chloride (31.78 g, 0.14 mol) and the mixture stirred at room temperature for 18 hours. The reaction mixture was then washed with 0.5 N HCl (0.40 L), water (2 times 0.40 L) and brine (0.25 L) and the organic phase dried over sodium sulphate and evaporated. The residue was sonicated in ether/dichloromethane 95:5 and the precipitate filtered and dried under vacuum. 1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid methyl ester was obtained as an off-white solid, 42.05 g (93%), MS (ISP): m/e=376.4 (M+H).

Workup

  1. washThe reaction mixture was then washed with 0.5 N HCl (0.40 L), water (2 times 0.40 L) and brine (0.25 L)
  2. dry with materialthe organic phase dried over sodium sulphate
  3. customevaporated
  4. customThe residue was sonicated in ether/dichloromethane 95:5
  5. filtrationthe precipitate filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c4a6d435aec04483bb9b8b2d6eda8fb7
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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