Ammonia → 3-nitro-5,6,7,8-tetrahydroquinoline

HRID 2289512노트

반응식

HRID 2289512 반응식
C[N:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[C:3]1=O.[C:15]1(=O)[CH2:20]CC[CH2:17][CH2:16]1.N>CO>[N+:8]([C:6]1[CH:7]=[N:2][C:3]2[CH2:20][CH2:15][CH2:16][CH2:17][C:4]=2[CH:5]=1)([O-:10])=[O:9]

참가 물질

5

반응물 3

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

생성물 1

HCID 110303733-nitro-5,6,7,8-tetrahydroquinoline수율 94.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 1-methyl-3,5-dinitro-2-pyridone (2.4 g, 0.012 mole), cyclohexanone (1.18 g, 0.012 mole) and ammonia solution (2.0M, 120 mL) in methanol was refluxed overnight. The solvent was removed in vacuo and rhe 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 (2.02 g, 94% yield).

후처리

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

출처 및 근거

ORD 기록
ord-50781e9ad5c14424aeeae9c75cffe3ff
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06093727

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