Sodium Hydroxide → HCID 22458538, compound

HRID 2185462Notes

Reaction equation

HRID 2185462 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:18]([O:20]CC)=[O:19])=[CH:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:18]([OH:20])=[O:19])=[CH:11]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22458611HCID 22458611, compound

Product 1

HCID 22458538HCID 22458538, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 6-benzylquinoline-3-carboxylate (C, 1.85 g) and 1 N sodium hydroxide solution (7 mL) in ethanol (10 mL) was refluxed for 1.5 hr. After the solvents were removed in vacuo, the residue was diluted with water and washed with ethyl ether. The aqueous layer was acidified with 1 N hydrochloric acid, and the precipitate was collected by filtration to afford the title compound (1.10 g) as a pale yellow powder: mp 203-205° C.; 1H NMR (400 MHz, CD3OD) δ 4.22 (s, 2H), 7.10-7.38 (m, 5H), 7.62-7.85 (m, 2H), 8.03 (d, J=8.6 Hz, 1H), 8.89 (s, 1H), and 9.33 (d, J=1.9 Hz, 1H).

Workup

  1. customAfter the solvents were removed in vacuo
  2. additionthe residue was diluted with water
  3. washwashed with ethyl ether
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ad8261b429b748049a691b8eb69ae276
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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