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

HRID 1457645노트

반응식

HRID 1457645 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a97e03f550f649e6b15c304bc73d3271
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849735

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