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

HRID 326606Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 22017385HCID 22017385, compound

Product 1

HCID 148427267-Ethyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acidYield 87.8%

Procedure

Treatment of methyl 7-ethyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.8 g, Example 3a) with sodium hydroxide (0.58 g) as described in Example 1c, gave 7-ethyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (0.66g), m.p. 271° C., δ (360 MHz, NaOD) 1.30 (3H, t, CH3), 2.81 (2H, q, CH2), 6.66 (1H, s, 3-H), 7.36 (1H, d, 6-H), 7.66 (1H, s, 8-H) and 8.11 (1H, d, 5-H), (Found: C, 66.46: H, 5.01; N, 6.59%, C12H11NO3 requires C, 66.35; H, 5.10: N, 6.45%).

Sources & evidence

ORD record: ord-201e1361e8f14fc5b9fee963ecc3ae6d
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270309

Reaction notes

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