Hydrochloric Acid → HCID 178487721, compound

HRID 393960Notes

Reaction equation

HRID 393960 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16]CC)=[O:15].Cl>[OH-].[Na+].O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178469633HCID 178469633, compound

Product 1

HCID 178487721HCID 178487721, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 23719242Sodium hydroxide--water (1/1/1)Solvent

Procedure

A suspension of ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate (12.0 g, 48 mmol) in 10% sodium hydroxide/water (200 mL) was heated at reflux for 1.5 hr. The reaction mixture was allowed to cool to ambient temperature and then made acidic (pH=3) by the dropwise addition of concentrated hydrochloric acid. The resulting precipitate was isolated by filtration, washed twice with water and then dried overnight in a vacuum oven at 80° C. to provide 10.4 g of 4-hydroxy-7-methoxyquinoline-3-carboxylic acid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hr
  3. customThe resulting precipitate was isolated by filtration
  4. washwashed twice with water
  5. customdried overnight in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-54cb84c291994fc9a200289c9b271ec8
Source dataset
uspto-grants-2004_10
Patent number
US06809203B2

Reaction notes

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