Water → HCID 23128168, compound

HRID 358693Notes

Reaction equation

HRID 358693 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[CH:13][CH:14]=2)[N:9]([CH3:20])[CH:8]=1.C(N(CC)CC)C.O>ClCCl>[CH3:1][S:2]([O:6][C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[CH:13][CH:14]=2)[N:9]([CH3:20])[CH:8]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23128141HCID 23128141, compound

Product 1

HCID 23128168HCID 23128168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (0.88 ml) was added to a stirred suspension of 3-hydroxy-7-methoxy-1-methyl-4quinolone (0.7 g) and triethylamine (2.4 ml) in dry dichloromethane (100 ml) at ambient temperature and the resultant solution stirred for 3 hours. Water (50 ml) was added and the layers separated. The dichloromethane layer was dried over magnesium sulphate and the solvent evaporated. The residue was purified by flash chromatography on a silica gel column eluted with dichloromethane:methanol (19:1) followed by crystallisation from acetonitrile:methanol (20:1, 10 ml) to give the novel compound 7-methoxy-1-methyl-4-oxo-1,4-dihydroquinol-3-yl methanesulphonate, m.p. 163°.

Workup

  1. customthe layers separated
  2. dry with materialThe dichloromethane layer was dried over magnesium sulphate
  3. customthe solvent evaporated
  4. customThe residue was purified by flash chromatography on a silica gel column
  5. washeluted with dichloromethane:methanol (19:1)
  6. customfollowed by crystallisation from acetonitrile:methanol (20:1, 10 ml)

Sources & evidence

ORD record
ord-6b57e867b2a449f8891cbb12f34ae26a
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

Loading…