Sodium Hydroxide → HCID 117701628, compound

HRID 1507441Notes

Reaction equation

HRID 1507441 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:13]([CH3:14])=[C:12]2[C:7]([C:8](=[O:33])[C:9]([CH3:32])=[C:10]([CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=4)[CH2:17][CH2:16]3)[O:11]2)=[CH:6][CH:5]=1>CO>[OH:3][C:4]1[C:13]([CH3:14])=[C:12]2[C:7]([C:8](=[O:33])[C:9]([CH3:32])=[C:10]([CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=4)[CH2:17][CH2:16]3)[O:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117701567HCID 117701567, compound

Product 1

HCID 117701628HCID 117701628, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A 1 N aqueous sodium hydroxide solution (4 mL) was added to a solution of methyl 4-{[4-(7-hydroxy-3,8-dimethyl-4-oxo-4H-chromen-2-yl)piperidin-1-yl]methyl}benzoate (140 mg, 0.33 mmol) obtained in Example 23-1 in methanol (4 mL), and the mixture was heated with stirring at a bath temperature of 50° C. for 4 hours. Methanol in the reaction solution was distilled off under reduced pressure. Then, a 1 N aqueous hydrochloric acid solution (4 mL) and water (10 mL) were added to the residue, and insoluble matter was collected by filtration to obtain 125 mg of the title compound (yield: 89%).

Workup

  1. temperaturethe mixture was heated
  2. distillationMethanol in the reaction solution was distilled off under reduced pressure
  3. additionThen, a 1 N aqueous hydrochloric acid solution (4 mL) and water (10 mL) were added to the residue, and insoluble matter
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-09e58b5f3f73450f812932262e7c69b7
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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