Triethylamine → 1-Methyl-4-oxo-1,4-dihydroquinol-3-yl 1-butanesulphonate

HRID 358670Notes

Reaction equation

HRID 358670 reaction equation
[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:13])[CH:3]=1.C(N(CC)CC)C.[CH2:21]([S:25](Cl)(=[O:27])=[O:26])[CH2:22][CH2:23][CH3:24]>ClCCl>[CH2:21]([S:25]([O:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:13])[CH:3]=1)(=[O:27])=[O:26])[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 5900784(1H)-Quinolinone, 3-hydroxy-1-methyl-

Product 1

HCID 231280791-Methyl-4-oxo-1,4-dihydroquinol-3-yl 1-butanesulphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Hydroxy-1-methyl-4-quinolone (3 g) was suspended in dichloromethane (200 ml), triethylamine (5.6 ml) was added to the suspension and the mixture was stirred at ambient temperature for hour. 1 -Butanesulphonyl chloride (2.6 ml) was added to the suspension, the mixture stirred for 90 minutes and then left to stand overnight. The resultant mixture was washed with water (400 ml), aqueous sodium hydroxide (1M, 400 ml) and then further water (3×300 ml). The dichloromethane layer was dried over magnesium sulphate and evaporated to give a solid which was crystallised from methanol (100 ml) to give the novel compound 1-methyl-4-oxo-1,4-dihydroquinol-3-yl 1-butanesulphonate, m.p. 143°-144°.

Workup

  1. stirringthe mixture stirred for 90 minutes
  2. waitleft
  3. washThe resultant mixture was washed with water (400 ml), aqueous sodium hydroxide (1M, 400 ml)
  4. dry with materialThe dichloromethane layer was dried over magnesium sulphate
  5. customevaporated
  6. customto give a solid which
  7. customwas crystallised from methanol (100 ml)

Sources & evidence

ORD record
ord-fb8da9ab9d124799922b95279e548b65
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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