Sodium Hydroxide → 2-Hydroxy-6-nitroquinoline-3-carboxylic acid

HRID 1758482Notes

Reaction equation

HRID 1758482 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]([C:15]([O:17]CC)=[O:16])=[CH:7]2)([O-:3])=[O:2].[OH-].[Na+]>Cl>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]([C:15]([OH:17])=[O:16])=[CH:7]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131063286-Nitro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 131063292-Hydroxy-6-nitroquinoline-3-carboxylic acidYield 94.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 9.7 g (37 mmol) of the above ester and 200 ml of 1 N sodium hydroxide is heated on the steam bath for 11/4 hours. The resulting suspension is poured over ice and acidified with 250 ml of 1 N hydrochloric acid. The solid is collected by filtration and washed with water and ethanol to give 8.15 g of the title acid, mp>310°.

Workup

  1. temperatureis heated on the steam bath for 11/4 hours
  2. additionThe resulting suspension is poured over ice
  3. filtrationThe solid is collected by filtration
  4. washwashed with water and ethanol

Sources & evidence

ORD record
ord-597169aa722f4b2ea964ca286702bb35
Source dataset
uspto-grants-1983_02
Patent number
US04374138

Reaction notes

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