Methyl iodide → Methyl 2-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]benzoate

HRID 1582957

Reaction equation

HRID 1582957 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[C:8]([NH:14][CH2:15][CH3:16])=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)=O.[C:20]1(=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][C:22](=[O:30])[O:21]1.CI.[C:34](=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[C:7]3[C:8](=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=3)[N:14]([CH2:15][CH3:16])[C:22](=[O:30])[C:23]=2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=2[C:20]([O:21][CH3:34])=[O:31])[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12801Homophthalic anhydrideHCID 110549023-(3-Chlorobenzoyl)-2-ethylamino-6-methylpyridine

Product 1

HCID 12991197Methyl 2-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

After the reaction of 3-(3-chlorobenzoyl)-2-ethylamino-6-methylpyridine with isochroman-1,3-dione (75%) under heating, the compound obtained by usual work-up was reacted with methyl iodide in 2-butanone in the presence of potassium carbonate. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain methyl 2-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]benzoate as a yellow solid. MS: 433.

Workup

  1. temperatureunder heating
  2. customthe compound obtained by usual work-up
  3. custompurified in a usual manner

Sources & evidence

ORD record
ord-a612e152cc634790bb966fa1e53ed09b
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Linked notes

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