Sodium Hydroxide → HCID 178422427, compound

HRID 1096778Notes

Reaction equation

HRID 1096778 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][C:6]([C:13]([O:15]CC)=[O:14])=[C:5]2[OH:18].[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][C:6]([C:13]([OH:15])=[O:14])=[C:5]2[OH:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178469509HCID 178469509, compound

Product 1

HCID 178422427HCID 178422427, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 6-bromo-4-hydroxy-8-methyl-3-quinolinecarboxylate (1.89 g, 6.09 mmol) and 6 N NaOH (1.22 g, 30.45 mmol, 5.1 mL) in ethanol (30 mL) was heated at reflux for 2.0 h and concentrated in vacuo. The residue was diluted with water and acidified with 6 N HCl to pH 4. The resulting solid was filtered, washed with water and diethyl ether, and dried overnight in a Buchner funnel to give the title compound (1.72 g, 99%) as a tan solid. MS(ES)+ m/e 282 [M+H].

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.0 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with water
  5. filtrationThe resulting solid was filtered
  6. washwashed with water and diethyl ether
  7. customdried overnight in a Buchner funnel

Sources & evidence

ORD record
ord-2d42ec0e8f954473b668744d34eeb05e
Source dataset
uspto-grants-2012_03
Patent number
US08138347B2

Reaction notes

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