Sodium Hydroxide → 7-Ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid

HRID 326620Notes

Reaction equation

HRID 326620 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:18])[CH:8]=[C:9]([C:13]([O:15]CC)=[O:14])[NH:10]2)=[CH:5][CH:4]=1)=[CH2:2].[OH-].[Na+]>O>[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:18])[CH:8]=[C:9]([C:13]([OH:15])=[O:14])[NH:10]2)=[CH:5][CH:4]=1)=[CH2:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19735194Ethyl 7-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

Product 1

HCID 148427277-Ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acidYield 76.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Treatment of ethyl 7-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.2 g) with sodium hydroxide (0.131 g), as described in Example 1c, gave 7-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (0.135 g), mp 281° C. (decomp.), δ (360 MHz, DMSO-d6), 5.47 and 6.00 (2H, 2d, =CH2), 6.61 (1H, s, 3-H), 6.84 (1H, 2d, CH=), 7.54 (1H, dd, 6-H), 7.94 (1H, d, 8-H), 8.05 (1H, d, 5-H) and 11.90 (1H, bs, NH), (Found: C, 63.76; H, 4.48; N, 6.12%, C12H9NO3. 0.6 H2O requires C, 63.77; H, 4.55; N, 6.20%).

Sources & evidence

ORD record
ord-50d7011db66f4552ab368c9ac9b2f4ad
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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