Methyl iodide → HCID 12669659, compound

HRID 1448567Notes

Reaction equation

HRID 1448567 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:5]2[C:14](=[O:21])[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:4]2=[C:3]1[C:22]#[N:23].IC.[C:26](=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>O.CN(C)C=O>[CH3:26][N:7]1[C:2](=[O:1])[C:3]([C:22]#[N:23])=[C:4]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14](=[O:21])[C:5]2=[C:6]1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12669653HCID 12669653, compound

Product 1

HCID 12669659HCID 12669659, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 25 parts of 3,9-dihydro-3,9-dioxo-1-phenyl-2H-indeno[2,1-c]pyridine-4-carbonitrile, 114 parts of iodomethane, 115 parts of potassium carbonate, and 475 parts of N,N-dimethylformamide is heated at 85° for 11/4 hours, then diluted with 1500 parts of water, followed by 100 parts of aqueous 5% sodium hydroxide. The deep tan precipitate which forms is filtered off, dried in air, and consecutively recrystallized from a mixture of chloroform and hexane, ethyl acetate, a mixture of ethyl acetate and chloroform, and acetonitrile to give 3,9-dihydro-2-methyl-3,9-dioxo-1-phenyl-2H-indeno-[2,1-c]pyridine-4-carbonitrile melting at approximately 255°-256°. The product has the formula ##STR15##

Workup

  1. temperatureis heated at 85° for 11/4 hours
  2. filtrationThe deep tan precipitate which forms is filtered off
  3. customdried in air
  4. customconsecutively recrystallized from a mixture of chloroform and hexane, ethyl acetate
  5. additiona mixture of ethyl acetate and chloroform, and acetonitrile

Sources & evidence

ORD record
ord-9fddfd21c1d044b9b46dfa32b21a5ae8
Source dataset
uspto-grants-1979_12
Patent number
US04180666

Reaction notes

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