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

HRID 33943

反応式

HRID 33943 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 532207N-(4-methoxyphenyl)pyridine-4-carboxamide収率 88%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
23 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-1d9c6cc5ff654151b13c4dd5eca8c035
出典データセット
uspto-grants-2008_09
特許番号
US07429665B2

関連ノート

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