Phosphorus oxychloride → 6-Methyl-N,N-dicyclopentylnicotinamide

HRID 981053

反応式

HRID 981053 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH:11]1([NH:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:15][CH2:14][CH2:13][CH2:12]1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:16]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)=[O:8])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 1378606-Methylnicotinic acidHCID 247671Dicyclopentylamine

生成物 1

HCID 200716326-Methyl-N,N-dicyclopentylnicotinamide収率 44.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a suspension of 6-methylnicotinic acid (1.37 g, 10 mmol) in toluene (10 ml), N,N-dicyclopentylamine (1.84 g, 12 mmol) was added To the homogenous solution obtained, phosphorus oxychloride (0.23 mL, 12 mmol) was injected in dropwise fashion. The reaction mixture was then immersed in an oil-bath at 130° C. and refluxed for 8 h. The reaction flask was cooled and stirred at room temperature. After 16h, the reaction was quenched with water and extracted in ethyl acetate. The organic layer was successively washed with aq. potassium carbonate, water and brine. After drying (MgSO4), the solvent was removed. The crude product (2.5 g) was chromatographed (silica gel, ethyl acetate/acetonitrile 100/1.5) to give the title compound (1.2 g, 44%). IR (KBr)1625, 1590, 1450, 1430, 1375, 1340, 1290, 1130, 840, 750 cm-1 ; 1H NMR (CDCl3) 1.4-2.35 (m, 16H), 2.57 (s, 3H), 3.6-3.9 (m,2H), 7.17 (d, J=8 Hz, 1H), 7.6 (dd,J=3,8 Hz, 1H), and 8.5 ppm (d,J=3 Hz,1H).

後処理

  1. additionwas added To the homogenous solution
  2. customobtained
  3. customThe reaction mixture was then immersed in an oil-bath at 130° C.
  4. temperaturerefluxed for 8 h
  5. temperatureThe reaction flask was cooled
  6. customAfter 16h, the reaction was quenched with water
  7. extractionextracted in ethyl acetate
  8. washThe organic layer was successively washed with aq. potassium carbonate, water and brine
  9. dry with materialAfter drying (MgSO4)
  10. customthe solvent was removed
  11. customThe crude product (2.5 g) was chromatographed (silica gel, ethyl acetate/acetonitrile 100/1.5)

出典と根拠

ORDレコード
ord-e957701b38974072ae9583c99c4acedf
出典データセット
uspto-grants-1991_02
特許番号
US04990518

関連ノート

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