Sodium Hydroxide → HCID 14842741, compound

HRID 326645Notes

Reaction equation

HRID 326645 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([I: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.ClC1C=C2C(C(=O)C=C(C(OCC)=O)N2)=C(I)C=1.[OH-].[Na+].ClC1C=C2C(C(=O)C=C(C(O)=O)N2)=C(I)C=1>>[Cl:1][C:2]1[CH:11]=[C:10]([I: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

5

Reactant 4

HCID 14798Sodium HydroxideHCID 100664237-chloro-5-iodo-4-oxo-1H-quinoline-2-carboxylic acidHCID 19735168HCID 19735168, compoundHCID 19735179HCID 19735179, compound

Product 1

HCID 14842741HCID 14842741, compound

Procedure

Treatment of a mixture of ethyl 5-chloro-7-iodo-4-oxo-1,4-dihydroquinoline-2-carboxylate and ethyl 7-chloro-5-iodo-4-oxo-1,4-dihydroquinoline-2-carboxylate (1.0 g) with sodium hydroxide as described in Example 1c, gave a mixture (0.930 g) of 5-chloro-7-iodo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid and 7-chloro-5-iodo-4-oxo-1,4-dihydroquinoline-2carboxylic acid. Chromatography of this mixture (0.150 g) on a reverse phase carbon-18 column gave 5-chloro-7-iodo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (11 mg), mp 275° C. (dec). δ (360 MHz, DMSO-d6) 6.55 (1H, s, 3-H), 7.62 (1H, d, 6-H), 8.34 (1H, d, 8-H) and 11.91 (1H, bs, NH).

Sources & evidence

ORD record
ord-eb9e66b7731743b288417b37cca4f92b
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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