Sodium Hydroxide → 5-Ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid

HRID 326619Notes

Reaction equation

HRID 326619 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:18])[CH:6]=[C:7]([C:13]([O:15]CC)=[O:14])[NH:8]2)=[CH2:2].[OH-].[Na+]>O>[CH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:18])[CH:6]=[C:7]([C:13]([OH:15])=[O:14])[NH:8]2)=[CH2:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19735212Ethyl 5-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

Product 1

HCID 148427185-Ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acidYield 70.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Treatment of ethyl 5-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.15 g) with sodium hydroxide (0.1 g), as described in Example 1c, gave 5-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (0.094 g), mp 265°-266° C., δ (360 MHz, DMSO-d6) 5.24 and 5.54 (2H, 2dd, =CH2), 6.56 (1H, s, 3-H), 7.37 (1H, d, 6-H), 7.62 (1H, t, 7-H), 7.91 (1H, d, 8-H), 8.17 (1H, 2d, CH=) and 11.80 (1H, bs, NH), (Found: C, 66.43; H, 4.37; N, 6.37%, C12H9NO3. 0.1 H2O requires C, 66.35; H, 4.36; N, 6.44%).

Sources & evidence

ORD record
ord-c8902ca891cc49c4add15773088917ba
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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