Methanol → HCID 23369691, compound

HRID 1900731Notes

Reaction equation

HRID 1900731 reaction equation
O[CH2:2][CH2:3][CH:4]1[O:18][C:7]2=[C:8]3[C:13](=[C:14]([CH3:16])[CH:15]=[C:6]2[CH2:5]1)[NH:12][C:11](=[O:17])[CH:10]=[CH:9]3.N1C=CC=CC=1.CS([Cl:29])(=O)=O.CO>CN(C)C=O.O>[Cl:29][CH2:2][CH2:3][CH:4]1[O:18][C:7]2=[C:8]3[C:13](=[C:14]([CH3:16])[CH:15]=[C:6]2[CH2:5]1)[NH:12][C:11](=[O:17])[CH:10]=[CH:9]3

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 23369640HCID 23369640, compound

Product 1

HCID 23369691HCID 23369691, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(2-Hydroxyethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (1.65 g) was suspended in dimethylformamide (20 ml). To the suspension, pyridine (20 ml) and methanesulfonyl chloride (1.5 ml) were added thereto, and the mixture was stirred for 6 hours. When the reaction was completed, methanol (20 ml) was added while cooling the mixture on ice, followed by mixing for 20 minutes. Subsequently, the reaction mixture was condensed under reduced pressure, to which water was added and extracted with chloroform. The chloroform phase was dried and condensed under reduced pressure. The resultant residue was recrystallized from a solvent mixture of chloroform-ether to obtain 1.75 of 2-(2-chloroethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one as pale yellow needles (98.6%).

Workup

  1. temperaturewhile cooling the mixture on ice
  2. additionby mixing for 20 minutes
  3. customcondensed under reduced pressure
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform phase was dried
  6. customcondensed under reduced pressure
  7. customThe resultant residue was recrystallized from a solvent mixture of chloroform-ether

Sources & evidence

ORD record
ord-5f9280c59c424bc9a6ca8352af9839f4
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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