Methanol → HCID 16660091, compound

HRID 2266610Notes

Reaction equation

HRID 2266610 reaction equation
C[O:2][C:3](=[O:32])[CH:4]([O:6][C:7]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]2[C:8]=1[C:9]([CH3:31])=[C:10]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])[C:11]([O:18][CH:19]([F:21])[F:20])=[N:12]2)[CH3:5].CO.[OH-].[Li+]>O>[Cl:30][C:24]1[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=1[CH2:22][C:10]1[C:11]([O:18][CH:19]([F:20])[F:21])=[N:12][C:13]2[C:8]([C:9]=1[CH3:31])=[C:7]([O:6][CH:4]([CH3:5])[C:3]([OH:32])=[O:2])[CH:16]=[CH:15][C:14]=2[F:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68781863HCID 68781863, compound

Product 1

HCID 16660091HCID 16660091, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[3-(2,4-dichlorobenzyl)-2-difluoromethoxy-8-fluoro-4-methylquinolin-5-yloxy]propionic acid methyl ester (0.15 g), methanol (5.0 mL), water (0.2 mL) and 5.0 M aqueous lithium hydroxide solution (0.090 mL) was stirred at room temperature for 24 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was acidified by the addition of glacial acetic acid and the resulting precipitate collected by filtration, washed with water and a mixture of water and methanol (1:1 by volume) and then dried to afford title compound as a white solid, 0.13 g.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was acidified by the addition of glacial acetic acid
  4. filtrationthe resulting precipitate collected by filtration
  5. washwashed with water
  6. additiona mixture of water and methanol (1:1 by volume)
  7. customdried

Sources & evidence

ORD record
ord-4c4452cc1aa84581a41259e653f795e8
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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