Methyl iodide → HCID 66583910, compound

HRID 242127Notes

Reaction equation

HRID 242127 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:18])=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([F:17])[CH:10]=2)=[O:5])[CH3:2].IC.[CH3:21]COC(C)=O.CCCCCC>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:18][CH3:21])=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([F:17])[CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 21226206Ethyl acetate hexaneHCID 178470063HCID 178470063, compound

Product 1

HCID 66583910HCID 66583910, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2.30 g (9.24 mmol) 7-fluoro-2-hydroxy-4-methylquinoline-3-carboxylic acid ethyl ester in DCM (60 ml) were added 6.36 g (23.1 mmol) Ag2CO3 and 1.44 ml (23.1 mmol) iodomethane at RT. The reaction mixture was stirred at RT for 16 h. Then the mixture was filtered through celite and the filtrate was concentrated in vacuum. After CC (EtOAc/hexane 1:4) of the residue, 1.50 g (5.70 mmol, 62%) 7-fluoro-2-methoxy-4-methylquinoline-3-carboxylic acid ethyl ester were obtained.

Workup

  1. filtrationThen the mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-e3e456cd6edb4b52aeba57bb9f3a6c91
Source dataset
uspto-grants-2014_02
Patent number
US08653101B2

Reaction notes

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