4-Toluenesulfonyl chloride → 2-(Chloromethyl)-6-methylquinoline

HRID 1062499Notes

Reaction equation

HRID 1062499 reaction equation
C1(C)C=CC(S([Cl:10])(=O)=O)=CC=1.[CH3:12][C:13]1(C)[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH3:23])[CH:19]=2)[NH+:14]1[O-]>ClC(Cl)C>[Cl:10][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH3:23])[CH:19]=2)[N:14]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 865882432,6-Dimethylquinaldine N-oxide

Product 1

HCID 147504892-(Chloromethyl)-6-methylquinolineYield 60%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring solution of p-toluenesulfonyl chloride (6.19 g, 0.0325 mol) in dichloroethane (75 mL) was added 2,6 dimethylquinaldine N-oxide (2) (5 g, 0.0289 mol) under N2. The reaction mixture was then heated to 100° C. for 24 hours, cooled, concentrated and extracted with 10% K2CO3 and ethyl acetate. The organic layer was dried with MgSO4, concentrated and purified on a small silica flash column (2:1 dichloromethane:hexanes). The resulting yellow solid was then recrystallized in hexanes to afford 3.31 g (60%) of a white solid. H1 NMR (CDCl3): δ 2.50 (s, 3H) 4.80 (s, 2H), 7.40-7.50 (m, 2H), 7.58-7.61 (d, 1H), 8.02-8.99 (m, 1H), 8.11-8.14 (d, 1H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. extractionextracted with 10% K2CO3 and ethyl acetate
  4. dry with materialThe organic layer was dried with MgSO4
  5. concentrationconcentrated
  6. custompurified on a small silica flash column (2:1 dichloromethane:hexanes)
  7. customThe resulting yellow solid was then recrystallized in hexanes

Sources & evidence

ORD record
ord-8f4e3ff977fd4f928adfa7489f611d34
Source dataset
uspto-grants-2005_11
Patent number
US06962690B2

Reaction notes

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