Dichloromethane → 1,4-Dihydro-3-methoxymethyl-5-methyl-8-nitro-4-oxoquinoline

HRID 613565Notes

Reaction equation

HRID 613565 reaction equation
[OH:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=[CH:9][C:10]=2[CH3:14])[NH:5][CH:4]=1.S(Cl)(Cl)=O.Cl[CH2:23]Cl>>[CH3:23][O:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=[CH:9][C:10]=2[CH3:14])[NH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 24386Thionyl ChlorideHCID 195924831,4-Dihydro-3-hydroxymethyl-5-methyl-8-nitro-4-oxoquinoline

Product 1

HCID 195923511,4-Dihydro-3-methoxymethyl-5-methyl-8-nitro-4-oxoquinoline

Procedure

To a suspension of 1,4-dihydro-3-hydroxymethyl-5-methyl-8-nitro-4-oxoquinoline (1.12 g) in dichloromethane (10 ml) was dropwise added a solution of thionyl chloride (569 mg) in dichloromethane (5 ml) under ice-cooling, and the mixture was stirred for 1 hour at the same temperature and for 2 hours at ambient temperature. The mixture was concentrated in vacuo, suspended in dichloromethane-methanol and refluxed for 2 hours. The mixture was evaporated in vacuo, and the residue was recrystalized from methanol to give 1,4-dihydro-3-methoxymethyl-5-methyl-8-nitro-4-oxoquinoline (889 mg).

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated in vacuo
  3. temperaturerefluxed for 2 hours
  4. customThe mixture was evaporated in vacuo
  5. customthe residue was recrystalized from methanol

Sources & evidence

ORD record
ord-95f2cf7a6b9d4cbdad2eb0d93b8ffbf2
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…