Sodium Hydroxide → HCID 14842739, compound

HRID 326649Notes

Reaction equation

HRID 326649 reaction equation
[I:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:18])[CH:5]=[C:6]([C:13]([O:15]CC)=[O:14])[NH:7]2.IC1C=C2C(C(=O)C=C(C(OCC)=O)N2)=C(C)C=1.[OH-].[Na+]>>[I:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:18])[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[NH:7]2

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 19735205HCID 19735205, compoundHCID 19735208HCID 19735208, compound

Product 1

HCID 14842739HCID 14842739, compound

Procedure

Treatment of a mixture of ethyl 5-iodo-7-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate and ethyl 7-iodo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.449 g) with sodium hydroxide (0.20 g) as described in Example 1c gave a mixture of the corresponding carboxylic acids. Chromatography of this mixture (0.220 g) on a reverse phase carbon-18 column gave 5-iodo-7-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (12 mg), mp 306° C. δ (360 MHz, DMSO-d6) 2.33 (3H, s, CH3), 6.55 (1H, s, 3-H) and 7.75 (2H, bs, 6-H and 8-H).

Workup

  1. customgave

Sources & evidence

ORD record
ord-a696a987d30d4ea8bf14647cb2c2d3c4
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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