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

HRID 1287857ノート

反応式

HRID 1287857 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
110 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-615754386bef4a4399f91feb0d0c42a6
出典データセット
uspto-grants-1976_10
特許番号
US03985888

反応ノート

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