Methanol → 6-[([1,1'-Biphenyl]-2-carbonyl)amino]pyridine-3-carboxylic acid

HRID 863043Notes

Reaction equation

HRID 863043 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:2]([C:7]([NH:9][C:10]2[N:15]=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][CH:11]=2)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.CO.[OH-].[Na+]>O1CCCC1>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:2]([C:7]([NH:9][C:10]2[N:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][CH:11]=2)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22099771Methyl 6-[([1,1'-biphenyl]-2-carbonyl)amino]-pyridine-3-carboxylate

Product 1

HCID 220997396-[([1,1'-Biphenyl]-2-carbonyl)amino]pyridine-3-carboxylic acidYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2.5 g of methyl 6-[([1,1'-Biphenyl]-2-carbonyl)amino]-pyridine-3-carboxylate in 50 ml of 1:1 tetrahydrofuran:methanol is added 10 ml of 5N sodium hydroxide and the mixture stirred at room temperature for 16 hours. The reaction mixture is concentrated in vacuo to a residue which is dissolved in water and neutralized with acetic acid. The separated colorless solid is filtered and air dried to give 2.0 g of the desired product: M+=318.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo to a residue which
  2. dissolutionis dissolved in water and neutralized with acetic acid
  3. filtrationThe separated colorless solid is filtered
  4. customair dried

Sources & evidence

ORD record
ord-ea88c174b32a4e23a8df408c620b3665
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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