Sodium Hydroxide → 2-Hydroxyquinoline-5-carboxylic acid

HRID 1262839

Reaction equation

HRID 1262839 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[NH:7][C:8](=[O:14])[CH:9]=[CH:10]OCC)([OH:3])=[O:2].[OH-].[Na+]>S(=O)(=O)(O)O>[C:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:6]2[C:5]=1[CH:10]=[CH:9][C:8](=[O:14])[NH:7]2)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 545354873-[(3-Ethoxyacryloyl)amino]benzoic acid

Product 1

HCID 132429962-Hydroxyquinoline-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

8 Grams of m-carboxy-N-(β-ethoxyacryloyl)aniline was added in 80 ml of concentrated sulfuric acid and stirred at a room temperature for 2 hours, then stirred at 50° C. for 1 hour. The reaction mixture was poured into ice and the pH of the mixture was adjusted to pH 3-4 by adding 10 N-sodium hydroxide aqueous solution. The precipitated crystals were collected by filtration and washed with water, recrystallized from dimethylformamide to obtain 4.26 g of 5-carboxycarbostyril.

Workup

  1. stirringstirred at 50° C. for 1 hour
  2. additionThe reaction mixture was poured into ice
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-c6b23f842dcf4fb787cfe03b5f132162
Source dataset
uspto-grants-1984_06
Patent number
US04454130

Linked notes

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