Ethanol → 1-methyl-4-(2-methylphenyl)-2-oxo-1,2,7,8-tetrahydro-6H-cyclopenta[g]quinoline-3-carboxylic acid

HRID 36939Notes

Reaction equation

HRID 36939 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH2:14][CH2:13][CH2:12][C:9]=3[CH:10]=2)[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[C:4]([C:22]([O:24]CC)=[O:23])[C:3]1=[O:27].[OH-].[K+].C(O)C>O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH2:14][CH2:13][CH2:12][C:9]=3[CH:10]=2)[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[C:4]([C:22]([OH:24])=[O:23])[C:3]1=[O:27]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 19936577HCID 19936577, compound

Product 1

HCID 152316201-methyl-4-(2-methylphenyl)-2-oxo-1,2,7,8-tetrahydro-6H-cyclopenta[g]quinoline-3-carboxylic acidYield 100.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 1-methyl-4-(2-methylphenyl)-2-oxo-1,2,7,8-tetrahydro-6H-cyclopenta[g]quinoline-3-carboxylate (2.0 g), potassium hydroxide (1.55 g) and 80% ethanol (20 ml) was stirred at 80° C. for 20 minutes. The mixture was diluted with water and acidified with 2N NCl to give crystals of 1-methyl-4-(2-methylphenyl) -2-oxo-1,2,7,8-tetrahydro-6H-cyclopenta[g]quinoline-3-carboxylic acid (1.85 g, 99.6%).

Sources & evidence

ORD record
ord-a15f8bd1a38044069caeeac901f8abb0
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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