Isonicotinic Acid → N-(4-methoxyphenyl)pyridine-4-carboxamide

HRID 33943

반응식

HRID 33943 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:17](O)(=[O:24])[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 5922Isonicotinic AcidHCID 7732P-AnisidineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydride

생성물 1

HCID 532207N-(4-methoxyphenyl)pyridine-4-carboxamide수율 88%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

반응 조건

온도
23 °C

실험 절차

A solution of p-anisidine (2.46 g, 20 mmol) and triethylamine (13.9 mL, 100 mmol) in ethyl acetate (200 mL) was treated with isonicotinic acid (2.46 g, 20 mmol) followed by 1-propanephosphonic acid cyclic anhydride (50% in ethyl acetate, 15.1 mL, 24 mmol). After stirring at 23° C. for 4 h, the reaction mixture was diluted with ethyl acetate, was washed with water and with brine, and the organic layer was dried (MgSO4), was filtered, and was concentrated in vacuo. Purification by silica gel chromatography with chloroform-methanol (40:1) gave 4 g (88% yield) of the title compound; diagnostic 13C NMR signals (100 MHz, CD3OD/CDCl3) δ 164.825, 157.213, 149.758, 143.349, 130.989, 123.085, 122.068, 55.285; MS (AP/Cl) 229.3 (M+H)+.

후처리

  1. washwas washed with water and with brine
  2. dry with materialthe organic layer was dried (MgSO4)
  3. filtrationwas filtered
  4. concentrationwas concentrated in vacuo
  5. customPurification by silica gel chromatography with chloroform-methanol (40:1)

출처 및 근거

ORD 기록
ord-1d9c6cc5ff654151b13c4dd5eca8c035
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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