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

HRID 361405

反応式

HRID 361405 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.[CH3:15][C:16]1(C)[CH2:20]C[CH2:18][C:17]1=O.N>CO>[CH3:15][C:16]1([CH3:20])[C:7]2=[N:2][CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]2[CH2:18][CH2:17]1

参加物

5

反応物 3

HCID 222AmmoniaHCID 1382862,2-DimethylcyclopentanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

生成物 1

HCID 234991895,6-Dihydro-7,7-Dimethyl-3-nitro-cyclopenta[b]pyridine収率 24%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 1-methyl-3,5-dinitro-2-pyridone (0.8 g, 4.0 mmol), 2,2-dimethyl-cyclopentanone (0.45 g, 4.0 mmol) and ammonia solution (2.0M) in methanol (40 mL) was refluxed overnight. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The soluble portion was flash chromatographed over silica gel (eluent 90:10 v/v ethyl acetate-hexane) to give a yellow solid (0.183 g, 24% yield).

後処理

  1. temperaturewas refluxed overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customchromatographed over silica gel (eluent 90:10 v/v ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-66ed24339d9542aeb83127d522d74002
出典データセット
uspto-grants-1999_02
特許番号
US05866579

関連ノート

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