Hydrochloric Acid → HCID 14842740, compound

HRID 326641Notes

Reaction equation

HRID 326641 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[CH:7]=[C:8]([C:12]([O:14]CC)=[O:13])[NH:9]2)=[C:4]([CH2:18][CH3:19])[CH:3]=1.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[CH:7]=[C:8]([C:12]([OH:14])=[O:13])[NH:9]2)=[C:4]([CH2:18][CH3:19])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19735198HCID 19735198, compound

Product 1

HCID 14842740HCID 14842740, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treatment of ethyl 7-chloro-5-ethyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (250 mg) with 2M is NAOH (1.5 ml) in DMF at room temperature for 76 h, followed by acidification with HCl, gave 7-chloro-5-ethyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (222 mg), mp 282°-283° C. δ (360 MHz, DMSO-d6) 1.15 (3H, t, CH3), 3.26 (2H, q, CH2), 6.55 (1H, s, 3-H), 7.10 (1H, d, 6-H), 7.88 (1H, d, 8-H) and 11.78 (1H, bs, NH).

Workup

  1. customat room temperature
  2. customfor 76 h

Sources & evidence

ORD record
ord-baadd79c22c04327a33e6b25c9e3c1c3
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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