Dimethylformamide → HCID 19936577, compound

HRID 36938Notes

Reaction equation

HRID 36938 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-l,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-a038ad7e81df4e2c86024dd8db18f4bc
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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