Hydrochloric Acid → 8-Cyclopropyl-4-ethoxyquinoline-2-carboxylic acid

HRID 545203Notes

Reaction equation

HRID 545203 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[C:9]([CH:14]3[CH2:16][CH2:15]3)[CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([C:17]([O:19]C)=[O:18])[CH:5]=1)[CH3:2].Cl>C(Cl)(Cl)Cl.CO>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[C:9]([CH:14]3[CH2:16][CH2:15]3)[CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([C:17]([OH:19])=[O:18])[CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57440905Methyl 8-cyclopropyl-4-ethoxyquinoline-2-carboxylate

Product 1

HCID 574408968-Cyclopropyl-4-ethoxyquinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

2.0 mL of 5N NaOHaq was added to a solution of 1.10 g of methyl 4-ethoxy-8-cyclopropylquinoline-2-carboxylate in 5 mL of CHCl3/MeOH (1:1) and the mixture was stirred at room temperature for 3 hr. After the addition of 3.0 mL of 5N HCl aq, the mixture was extracted by CHCl3. The organic layer was washed by satd. brine, dried over NaSO4, then concentrated to afford 4-ethoxy-8-cyclopropylquinoline-2-carboxylic acid as a colorless solid.

Workup

  1. extractionthe mixture was extracted by CHCl3
  2. washThe organic layer was washed by satd
  3. dry with materialbrine, dried over NaSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-399a332bf2274c59b2a4427fba84bce7
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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