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

HRID 1170382ノート

反応式

HRID 1170382 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/CI) 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-cb9ebf10226c459c87faf7af9b424872
出典データセット
uspto-grants-2010_11
特許番号
US07825254B2

反応ノート

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