Methyl iodide → HCID 57904058, compound

HRID 1518004Notes

Reaction equation

HRID 1518004 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[C:12]3[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([I:26])[CH:21]=2)=[O:8])=[CH:4][CH:3]=1.[CH3:27]I>O1CCCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+]>[Cl:1][C:2]1[S:6][C:5]([C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:27])[C:14](=[O:19])[CH:13]=[C:12]3[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([I:26])[CH:21]=2)=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 57904117HCID 57904117, compound

Product 1

HCID 57904058HCID 57904058, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

If one were to take 3 mmole of quinolone 5 from Step D dissolved in tetrahydrofuran (THF) and treat it with 1.5 equivalents of methyl iodide, 0.5 equivalents of benzyltriethylammonium chloride in 10 N aqueous sodium hydroxide and stir the resulting mixture for 24 hours followed by organic extraction with methylene chloride one would produce the resulting product, 6-(5-chloro-thiophene-2-carbonyl)-4-(3-iodo-phenyl)-1-methyl-1H-quinolin-2-one (6).

Workup

  1. extractionfollowed by organic extraction with methylene chloride one

Sources & evidence

ORD record
ord-906a189773a94f79b939163ad72ae919
Source dataset
uspto-grants-2012_07
Patent number
US08232402B2

Reaction notes

Loading…