4-Hydroxy-N-methylcarbostyril → 1-methyl-3-dimethylaminomethylene-(1H)-quinolin-2,4-dione

HRID 36043Notes

Reaction equation

HRID 36043 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]1=[O:13]>COC(OC)N(C)C.C(Cl)Cl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4](=[CH:1][N:2]([CH3:11])[CH3:3])[C:3]1=[O:13]

Participants

4

Reactant 1

HCID 546864364-Hydroxy-N-methylcarbostyril

Product 1

HCID 536541001-methyl-3-dimethylaminomethylene-(1H)-quinolin-2,4-dione

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A suspension of 1-methyl-4-hydroxy-2(1H)-quinolinone (1.0 gm) in dimethyl formamide dimethyl acetal (5 ml) and methylene chloride (2.0) was refluxed for 1 hour. The resulting dark orange solution was evaporated under reduced pressure to give 1-methyl-3-dimethylaminomethylene-(1H)-quinolin-2,4-dione.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customThe resulting dark orange solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1ebe7c35300644069711707db1ace0ff
Source dataset
uspto-grants-1995_05
Patent number
US05412104

Reaction notes

Loading…