Methanol → HCID 86718151, compound

HRID 2205169Notes

Reaction equation

HRID 2205169 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]3[C:11](=[CH:12][C:13]([C:25]([O:27]C)=[O:26])=[CH:14][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.[Li+].[OH-].CO>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]3[C:11](=[CH:12][C:13]([C:25]([OH:27])=[O:26])=[CH:14][CH:15]=3)[N:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86718150HCID 86718150, compound

Product 1

HCID 86718151HCID 86718151, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 2-(4-methoxyphenyl)-3-phenylquinoline-7-carboxylate (40 mg, 0.11 mmol, 1.00 equiv), LiOH (13 mg, 0.54 mmol, 5.00 equiv), methanol (5 mL), and water (0.5 mL) were placed in a 50-mL round-bottom flask and stirred for 5 hr at 50° C. in an oil bath. The resulting mixture was concentrated under vacuum, diluted with 10 mL of H2O, and the pH adjusted to 4-5 with 1N HCl. The resulting solids were collected by filtration and dried in an oven under reduced pressure, yielding 23 mg (59%) of 2-(4-methoxyphenyl)-3-phenylquinoline-7-carboxylic acid as a yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additiondiluted with 10 mL of H2O
  3. filtrationThe resulting solids were collected by filtration
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-0a1cb2dcca98403a837bb6497ea226ad
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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