Pyridine → 1-(5-Chloro-2-methoxy-benzenesulfonyl)-7-nitro-1,2,3,4-tetrahydro-quinoline

HRID 1715853Notes

Reaction equation

HRID 1715853 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.N1C=CC=CC=1.[N+:20]([C:23]1[CH:32]=[C:31]2[C:26]([CH2:27][CH2:28][CH2:29][NH:30]2)=[CH:25][CH:24]=1)([O-:22])=[O:21]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([S:8]([N:30]2[C:31]3[C:26](=[CH:25][CH:24]=[C:23]([N+:20]([O-:22])=[O:21])[CH:32]=3)[CH2:27][CH2:28][CH2:29]2)(=[O:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2525137-Nitro-1,2,3,4-tetrahydroquinolineHCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chloride

Product 1

HCID 684327391-(5-Chloro-2-methoxy-benzenesulfonyl)-7-nitro-1,2,3,4-tetrahydro-quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-chloro-2-methoxybenzenesulfonyl chloride (2.75 g, 11.20 mmol) in dichloromethane (0.15 L) was treated with pyridine (14.59 mL, 181.26 mmol) and a solution of 7-nitro-1,2,3,4-tetrahydro-quinoline (1.90 g, 10.66 mmol) in dichloromethane (6.00 mL). The mixture was stirred at room temperature for 120 hours, then the volatiles were evaporated. The residue was redissolved in dichloromethane and washed with water. The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography (dichloromethane/methanol gradient) to yield 1-(5-chloro-2-methoxy-benzenesulfonyl)-7-nitro-1,2,3,4-tetrahydro-quinoline as an orange solid, 3.46 g (85%), MS (ISP): m/e=383.1 (M+H).

Workup

  1. customthe volatiles were evaporated
  2. dissolutionThe residue was redissolved in dichloromethane
  3. washwashed with water
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by flash chromatography (dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-a3110554556d4e5f9b67e93e6b6e9ad9
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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