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

HRID 1457645Notes

Reaction equation

HRID 1457645 reaction equation
[C:1]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([N:9](C(C1C=CC=CC=1C1C=CC=CC=1)=O)[C:10]1[N:15]=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][CH:11]=1)=[O:8].[OH-].[Na+].C(O)(=O)C>CO.O1CCCC1>[C:1]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:9][C:10]1[N:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1)=[O:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 22099573Methyl 6-[[bis(2-biphenylcarbonyl)]amino]pyridine-3-carboxylate

Product 1

HCID 220997396-[([1,1'-Biphenyl]-2-carbonyl)amino]pyridine-3-carboxylic acidYield 89.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a chilled (0° C.) mixture of 6.0 g of methyl 6-[[bis[(1,1'-biphenyl]-2-ylcarbonyl)]amino]pyridine-3-carboxylate in 40 ml of methanol and 30 ml of tetrahydrofuran is added slowly 10 ml of 2N NaOH, The mixture is stirred at room temperature overnight and brought to pH 5 with glacial acetic acid. The mixture is concentrated, acidified to pH 2-3 with 1N HCl and extracted with 250 ml of ethyl acetate. The extract is washed with 50 ml of brine, dried (Na2SO4) and the solvent removed under vacuum. The residual white solid is triturated with 15 ml of ethyl acetate to give 3.35 g of white crystals, m.p. 215°-217° C.

Workup

  1. temperatureTo a chilled
  2. concentrationThe mixture is concentrated
  3. extractionextracted with 250 ml of ethyl acetate
  4. washThe extract is washed with 50 ml of brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed under vacuum
  7. customThe residual white solid is triturated with 15 ml of ethyl acetate

Sources & evidence

ORD record
ord-a97e03f550f649e6b15c304bc73d3271
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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