Dimethylformamide → HCID 19936577, compound

HRID 258046Notes

Reaction equation

HRID 258046 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][C:14]3[CH2:20][CH2:19][CH2:18][C:15]=3[CH:16]=2)[NH:11][C:10](=[O:21])[C:9]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].[C:27](=O)([O-])[O-].[K+].[K+].CN(C=O)C.CI>O>[CH3:27][N:11]1[C:12]2[C:17](=[CH:16][C:15]3[CH2:18][CH2:19][CH2:20][C:14]=3[CH:13]=2)[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[C:9]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]1=[O:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 19936582HCID 19936582, compound

Product 1

HCID 19936577HCID 19936577, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 4-(2-methylphenyl)-2-oxo-1,2,7,8-tetrahydro-6H-cyclopenta[g]quinoline-3-carboxylate (3.0 g), potassium carbonate (1.43 g) and DMF (30 ml) was added methyl iodide (0.65 ml) dropwise. The mixture was stirred at room temperature for 10 hours, after which water was added to the reaction mixture to give crystals of ethyl 1-methyl-4-(2-methylphenyl)-2-oxo-1,2,7,8-tetrahydro-6H-cyclopenta[g]quinoline-3-carboxylate (2.95 g, 94.6%). Recrystallization from ethyl ether-isopropyl ether gave colorless needles, m.p. 134°-135° C.

Sources & evidence

ORD record
ord-f90ff317ffa94271a0598eb086a7955d
Source dataset
uspto-grants-1993_11
Patent number
US05264454

Reaction notes

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