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

HRID 326611Notes

Reaction equation

[CH2:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:20])[CH:10]=[C:11]([C:15]([O:17]CC)=[O:16])[NH:12]2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>>[CH2:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:20])[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[NH:12]2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 19735204Ethyl 7-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

Product 1

HCID 148427307-Butyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acidYield 66.9%

Procedure

Treatment of ethyl 7-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.5 g, Example 5b) with sodium hydroxide (0.326 g), as described in Example 1c, gave 7-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (0.3 g), mp 247°-250° C. (decomp), δ (360 MHz, DMSO-d6) 0.91 (3H, t, CH3), 1.32 (2H, m, CH2CH3), 1.60 (2H, m, CH2CH2CH2), 2.69 (2H, t, CH2CH2CH2CH3), 6.60 (1H, s, 3-H), 7.20 (1H dd, 6-H), 7.75 (1H, s, 8-H) and 7.98 (1H, d. 5-H), (Found: C, 66.44; H, 6.68; N, 5.62%. C14H15NO3. 0.5H2O requires C, 66.13; H, 6.34; N, 5.51%).

Sources & evidence

ORD record: ord-6f1f76a73f7743cd9182ba361701621c
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270309

Reaction notes

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