Diazomethane → 2,3,6,7,8,9-Hexahydro-2-methoxymethyl-5-methylfuro-[2,3-f]quinoline-7-one

HRID 1900721Notes

Reaction equation

HRID 1900721 reaction equation
[OH:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH2:9][CH2:8]3.[N+](=[CH2:20])=[N-]>O1CCCC1.CCOCC>[CH3:20][O:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH2:9][CH2:8]3

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 233697232,3,6,7,8,9-Hexahydro-2-hydroxymethyl-5-methylfuro[2,3-f]quinoline-7-one

Product 1

HCID 233695592,3,6,7,8,9-Hexahydro-2-methoxymethyl-5-methylfuro-[2,3-f]quinoline-7-oneYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3,6,7,8,9-hexahydro-2-hydroxymethyl -5-methylfuro-[2,3-f]quinoline-7-one (300 mg) in tetrahydrofuran (100 ml), silica gel (10 g) and a solution of diazomethane in ether (200 ml) were added, and stirred at room temperature for 36 hours. After completion of the reaction, the solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 280 mg of the target product as a pale yellow powder (88%).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5075a3aa231b46298c541fe949785e92
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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