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

HRID 1597354노트

반응식

HRID 1597354 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 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 (2.02 g, 94% 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-fdc1b675e618444bbdd94a55b73448ae
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06294566B1

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