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

HRID 326610Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 19735225Ethyl 5-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

Product 1

HCID 148427215-Butyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acidYield 89.1%

Procedure

Treatment of ethyl 5-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.5 g) with sodium hydroxide (0.293 g), as described in Example 1c, gave 5-butyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (0.4 g), mp 269°-270° C., δ (360 MHz, DMSO-d6) 0.89 (3H, t, CH3), 1.53 (2H, m, CH2CH3), 1.49 (2H, m, CH2CH2CH2), 3.25 (2H, t, CH2CH2CH2), 6.53 (1H, s, 3-H), 7.03 (1H, dd, 6-H), 7.50 (1H, t, 7-H) and 7.78 (1H, dd, 8-H), (Found: C, 67.55; H, 6.60: N, 5.88%, C14H15NO3. 0.2H2O requires C, 67.56; H, 6.24, N, 5.62%).

Sources & evidence

ORD record: ord-b2c4f6ad917e4009817943e2d870b184
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270309

Reaction notes

Loading…