3,4-Dimethoxybenzeneacetonitrile → 2,3-dihydro-6,7-dimethoxyspiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione

HRID 1287857노트

반응식

HRID 1287857 반응식
[C:1]([C:3]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)([CH2:10][CH2:11][C:12]([O:14]C)=O)[CH2:4][CH2:5][C:6]([O:8]C)=O)#[N:2].C[O:27]C1C=C(CC#N)C=CC=1OC>>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[O:24][CH3:25])[C:3]1([CH2:10][CH2:11][C:12](=[O:14])[NH:2][C:1]1=[O:27])[CH2:4][CH2:5][C:6]2=[O:8]

참가 물질

3

반응물 2

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 1803855Dimethyl 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioate

생성물 1

HCID 215067812,3-dihydro-6,7-dimethoxyspiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione수율 18%

반응 조건

온도
110 °C

실험 절차

Unpurified dimethyl γ-cyano-γ-(3,4-dimethoxyphenyl)pimelate, prepared from 334 grams of 3,4-dimethoxyphenylacetonitrile as described by Horning et al., J. Am. Chem. Soc., 74, 773 (1942), was added with stirring to 3.0 kg of polyphosphoric acid. This reaction mixture was stirred at 110° C. for 2 hours and poured into 6.0 liters of crushed ice with stirring. The resulting solid was filtered and recrystallized from isopropyl alcohol-water to give 65.8 grams (18%) of 2,3-dihydro-6,7-dimethoxyspiro-[naphthalene-1(4H),3'-piperidine]-2',4,6'-trione, melting point 269°-271° C.

후처리

  1. addition, 74, 773 (1942), was added
  2. stirringwith stirring
  3. filtrationThe resulting solid was filtered
  4. customrecrystallized from isopropyl alcohol-water

출처 및 근거

ORD 기록
ord-615754386bef4a4399f91feb0d0c42a6
출처 데이터셋
uspto-grants-1976_10
특허 번호
US03985888

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