Methyl iodide → HCID 19735181, compound

HRID 326665Notes

Reaction equation

HRID 326665 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]2[C:5]=1[C:6](=[O:23])[CH:7]=[C:8]([C:15](=[O:22])[NH:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[NH:9]2.[CH3:24][I:25]>CN(C)C=O>[I-:25].[Cl:3][C:4]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]2[C:5]=1[C:6](=[O:23])[CH:7]=[C:8]([C:15](=[O:22])[NH:16][CH2:17][CH2:18][N+:19]([CH3:24])([CH3:20])[CH3:21])[NH:9]2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 19735156HCID 19735156, compound

Product 1

HCID 19735181HCID 19735181, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5,7-dichloro-2-(2-dimethylaminoethyl)carbamoyl-4-oxo-1,4-dihydroquinoline (0.5 g, Example 39) in dry dimethylformamide was added methyl iodide and the mixture was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure to yield the crude product, which was recrystallised from ethanol-water to give 5,7-dichloro-2-(2-trimethylammonioethyl)carbamoyl-4-oxo-1,4-dihydroquinoline iodide (0.39 g), m.p.>280° C. δ (360 MHz, D2O) 3.26 (9H, s, (CH3)3), 3.62 (2H, t, CH2N), 3.94 (2H, t, CONHCH2), 6.78 (1H, s, 3-H), 7.50 (1H, d, 6-H) and 7.76 (1H, d, 8-H), (Found: C, 37.06; H, 3.91; N, 8.65; I, 26.14%. C15H18Cl2IN3O2 requires C, 36.98; H, 3.91; N, 8.62; I, 26.02%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto yield the crude product, which
  3. customwas recrystallised from ethanol-water

Sources & evidence

ORD record
ord-1cee930c1dd7441da2348b28dccfea13
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

Loading…