Lithium Hydroxide → HCID 178418698, compound

HRID 348065Notes

Reaction equation

HRID 348065 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:16])=[CH:7][C:8]([C:12]([O:14]C)=[O:13])=[N:9]2)=[CH:4][CH:3]=1.[Li+].[OH-]>CO.O>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:16])=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178419010HCID 178419010, compound

Product 1

HCID 178418698HCID 178418698, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

7-methyl-4-hydroxy-2-methoxycarbonylquinoline (6.45 g, 30.14 mmol) was suspended in MeOH (150 mL) and water (100 mL), and LiOH (3.08 g, 75.5 mmol) was added and stirred at ambient temperature for 2 hours. The methanol was evaporated in vacuo and residue was crystallized by addition of 2N hydrochloric acid. The resulting solid was filtered, washed with water and dried to afford 7-methyl-4-hydroxy-2-carboxyquinoline (6.0 g, 98%), NMR (DMSO-d6) 2.40 (s, 3), 6.68 (s, 1), 7.22 (d, 1), 7.68 (s, 1), 7.96 (d, 1).

Workup

  1. customThe methanol was evaporated in vacuo and residue
  2. customwas crystallized by addition of 2N hydrochloric acid
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9019f4087fa0408cb9b6009a8be60175
Source dataset
uspto-grants-2007_02
Patent number
US07176207B2

Reaction notes

Loading…