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

HRID 361405

반응식

HRID 361405 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-66ed24339d9542aeb83127d522d74002
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866579

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