Methanesulfonyl chloride → HCID 77231181, compound

HRID 1804627Notes

Reaction equation

HRID 1804627 reaction equation
[N:1]1[C:10]2[CH:9]([OH:11])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>CN(C)C1C=CN=CC=1.ClCCl.O>[CH3:12][S:13]([O:11][CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)(=[O:15])=[O:14]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 118159398-Hydroxy-5,6,7,8-tetrahydroquinoline

Product 1

HCID 77231181HCID 77231181, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2.0 g (13 mmol) of 5,6,7,8-tetrahydroquinolin-8-ol and 3.3 g (27 mmol) of 4-(dimethylamino)pyridine in 30 mL of dichloromethane was added 1.3 mL (16 mmol) of methanesulfonyl chloride under an atmosphere of nitrogen. The reaction mixture was stirred for 8 h and then diluted with 30 mL water. The aqueous phase was then extracted with dichloromethane (3×30 mL) and the combined organics were dried over magnesium sulfate, filtered and evaporated in vacuo to afford the title compound as a light orange gum that was used without further purification. LC/MS: m/z (ES) 172.0 (MH)+.

Workup

  1. extractionThe aqueous phase was then extracted with dichloromethane (3×30 mL)
  2. dry with materialthe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-1e47f5ffad8b4eb983b92654be690075
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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