Lithium Hydroxide → HCID 178418698, compound

HRID 890381Notes

Reaction equation

HRID 890381 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 887MethanolSolvent2×HCID 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. customwas 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-2f38b8b6492d46d6a35300effa05ad21
Source dataset
uspto-grants-2006_02
Patent number
US06995156B2

Reaction notes

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