Methyl iodide → HCID 18523248, compound

HRID 413049Notes

Reaction equation

HRID 413049 reaction equation
[F:1][C:2]1[C:15]2[N:14]=[CH:13][C:12]3[NH:11][CH:10]=[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8](=[O:21])[C:7]=3[C:6]=2[CH:5]=[CH:4][C:3]=1[F:22].[C:23](=O)([O-])[O-].[K+].[K+].CI>CS(C)=O>[F:1][C:2]1[C:15]2[N:14]=[CH:13][C:12]3[N:11]([CH3:23])[CH:10]=[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8](=[O:21])[C:7]=3[C:6]=2[CH:5]=[CH:4][C:3]=1[F:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18523347Ethyl 7,8-difluoro-1,4-dihydro-1-oxobenzo[f][1,7]naphthyridine-2-carboxylate

Product 1

HCID 18523248HCID 18523248, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 35 g of ethyl 7,8-difluoro-1-oxo-1,4-dihydrobenzo[f][1,7]-naphthyridine-2-carboxylate and 31.8 g of potassium carbonate in 350 cm3 of dimethyl sulphoxide was heated, with stirring, at a temperature of 90° C. for 3 hours. After cooling to 50° C., 65 g of methyl iodide were added; the mixture was heated at 90° C. for 3 hours. After cooling to 20° C., the insoluble material was dewatered, washed 4 times with 100 cm3 of water, 3 times with 100 cm3 of ethanol, and twice with 100 cm3 of diethyl ether. 25.5 g of ethyl 7,8-difluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylate was obtained in the form of white crystals, which melted at 320° C.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling to 50° C.
  3. temperaturethe mixture was heated at 90° C. for 3 hours
  4. temperatureAfter cooling to 20° C.
  5. washwashed 4 times with 100 cm3 of water, 3 times with 100 cm3 of ethanol

Sources & evidence

ORD record
ord-179f98dba06644a0b17f8182fdb7f904
Source dataset
uspto-grants-2003_05
Patent number
US06566362B2

Reaction notes

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