Ethanol → 4'-Methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)biphenyl-3-carboxylic acid

HRID 1845212Notes

Reaction equation

HRID 1845212 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14](=[O:24])[NH:15][CH2:16][C:17]3[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=3)[CH:11]=[C:10]([C:25]([O:27]CC)=[O:26])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].CCO>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14](=[O:24])[NH:15][CH2:16][C:17]3[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=3)[CH:11]=[C:10]([C:25]([OH:27])=[O:26])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 58188105Ethyl 4'-methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)biphenyl-3-carboxylate

Product 1

HCID 581880514'-Methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 4′-methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)biphenyl-3-carboxylate (1.02 g, 2.62 mmol), lithium hydroxide (310 mg, 13 mmol), EtOH (100 mL), and water (10 mL) was stirred at rt overnight. LC-MS indicated completion of the reaction. The solvent was removed in vacuo and the residue was treated with water (50 mL) and acidified with 1N aq. HCl to pH=4. The precipitated solids were collected by filtration, washed with water, and dried to yield a white solid.

Workup

  1. customcompletion of the reaction
  2. customThe solvent was removed in vacuo
  3. additionthe residue was treated with water (50 mL)
  4. filtrationThe precipitated solids were collected by filtration
  5. washwashed with water
  6. customdried
  7. customto yield a white solid

Sources & evidence

ORD record
ord-22139c25d95041a98bf61f4168e24a0c
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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