Hydrochloric Acid → HCID 57742536, compound

HRID 2266491Notes

Reaction equation

HRID 2266491 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([CH3:29])=[C:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:10]([O:17][CH:18]([F:20])[F:19])=[N:11]2.O1CCCC1.[OH-].[Li+].Cl>CO>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C:9]2[C:10]([O:17][CH:18]([F:19])[F:20])=[N:11][C:12]3[C:7]([C:8]=2[CH3:29])=[C:6]([O:5][CH2:4][C:3]([OH:30])=[O:2])[CH:15]=[CH:14][C:13]=3[F:16])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68785003HCID 68785003, compound

Product 1

HCID 57742536HCID 57742536, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [3-(4-chlorobenzyl)-2-difluoromethoxy-8-fluoro-4-methylquinolin-5-yloxy]acetic acid methyl ester (0.45 g), tetrahydrofuran (5.0 mL), methanol (5.0 mL) and 1.0 M aqueous lithium hydroxide solution (1.3 mL) was stirred at room temperature for 18 hours. The solution was acidified by the addition of 1.0 M aqueous hydrochloric acid and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. Crystallisation of the residue from a mixture of water and propan-2-ol gave title compound as a white solid, 0.33 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customthe solvent removed under reduced pressure
  4. customCrystallisation of the residue
  5. additionfrom a mixture of water and propan-2-ol

Sources & evidence

ORD record
ord-f5cbb573ff4b4a3d8bf523c5985d8d11
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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