Triethylamine → HCID 23128120, compound

HRID 358700Notes

Reaction equation

HRID 358700 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:20])[C:13]([OH:19])=[CH:14][N:15]2[CH3:18])=[CH:10][CH:9]=1)#[N:7].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:19][C:13]1[C:12](=[O:20])[C:11]2[C:16](=[CH:17][C:8]([C:6]#[N:7])=[CH:9][CH:10]=2)[N:15]([CH3:18])[CH:14]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23128113HCID 23128113, compound

Product 1

HCID 23128120HCID 23128120, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (1.0 ml) was added to a stirred suspension of 7-cyano-3-hydroxy-1-methyl-4quinolone (0.4 g) and triethylamine (2.0 ml) in dry dichloromethane (200 ml) at 0 to 5° and the resultant solution stirred for 2 hours. The solution was washed with water (2×50 ml), dried over magnesium sulphate and the solvent removed by distillation. The residue was purified by flash chromatography on a silica gel column eluted with dichloromethane:methanol (40:1) followed by trituration with diethyl ether (10 ml) to give the novel compound 7-cyano-1-methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate, m.p. 268°.

Workup

  1. washThe solution was washed with water (2×50 ml)
  2. dry with materialdried over magnesium sulphate
  3. customthe solvent removed by distillation
  4. customThe residue was purified by flash chromatography on a silica gel column
  5. washeluted with dichloromethane:methanol (40:1)

Sources & evidence

ORD record
ord-e4c193e8be114f13b1b399bc40f15691
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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