Ammonia → 6,7-Dihydro-3-nitro-5H-cyclopenta[b]pyridine

HRID 571977ノート

反応式

HRID 571977 の反応式
C[N:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]1=O.[C:15]1(=O)[CH2:20]CCC[CH2:16]1.N>CO>[N+:11]([C:4]1[CH:5]=[C:6]2[CH2:20][CH2:15][CH2:16][C:7]2=[N:2][CH:3]=1)([O-:13])=[O:12]

参加物

5

反応物 3

HCID 222AmmoniaHCID 7967CyclohexanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

生成物 1

HCID 115645226,7-Dihydro-3-nitro-5H-cyclopenta[b]pyridine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

A mixture of 1-methyl-3,5-dinitropyridin-2(1H)-one (B) (947 mg, 4.76 mmol), cyclohexanone (0.5 mL, 5.70 mmol) and ammonia solution (1 M) in methanol (50 mL) was heated to 70° C. for 3 h under N2. TLC showed complete consumption of starting material. The reaction mixture was removed in vacuo and extracted with ethyl acetate. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford 3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine (C). (340 mg, 44%)

後処理

  1. customconsumption of starting material
  2. customThe reaction mixture was removed in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude which
  8. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-c95e8641559d4568af478e97e65bf5da
出典データセット
uspto-grants-2015_05
特許番号
US09029378B2

反応ノート

読み込み中…