Hydrochloride methanol → HCID 178498588, compound

HRID 234284Notes

Reaction equation

HRID 234284 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:15]O.Cl>>[OH:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 178524625HCID 178524625, compound

Product 1

HCID 178498588HCID 178498588, compound

Procedure

To 2-hydroxyquinoline-4-carboxylic acid (V. 5.52 g) is added a saturated methanol/hydrochloric acid mixture in 50 ml aliquots over 5 days. The methanol/hydrochloric acid is then removed under reduced pressure and the residue is carefully treated with aqueous sodium bicarbonate. When the aqueous layer tests basic, the solid is collected, washed with water, and dried under reduced pressure to give methyl 2-hydroxyquinoline-4-carboxylate (VI), mp 240°-241°.

Workup

  1. customThe methanol/hydrochloric acid is then removed under reduced pressure
  2. additionthe residue is carefully treated with aqueous sodium bicarbonate
  3. customWhen the aqueous layer tests basic, the solid is collected
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-6a0f80de1edd4528898bd2133a510a45
Source dataset
uspto-grants-1997_01
Patent number
US05594140

Reaction notes

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