Ammonia → HCID 16100402、化合物

HRID 2276942ノート

反応式

HRID 2276942 の反応式
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[C:5]=1[CH2:13][C:14]#[N:15])#N.N>C(O)C.[Ni]>[O:10]1[C:6]2[C:5]3[CH2:13][CH2:14][NH:15][CH2:1][CH2:3][C:4]=3[CH:12]=[CH:11][C:7]=2[O:8][CH2:9]1

参加物

5

反応物 2

HCID 222AmmoniaHCID 161004012,2'-(2H-1,3-Benzodioxole-4,5-diyl)diacetonitrile

生成物 1

HCID 16100402HCID 16100402、化合物

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

(5-Cyanomethyl-1,3-benzodioxol-4-yl)acetonitrile (6.00 g, 30.0 mmoles) from Example 58C was reductively cyclized with Raney-Nickel (1.21 g) under a hydrogen atmosphere and high pressure (1100 p.s.i.) in a 10% ammonia in ethanol solution (121 mL) at 100° C. for one hour. The mixture was cooled, and the catalyst filtered off and washed with hot ethanol. The mixture was concentrated under reduced pressure, and the residue purified by normal phase HPLC on a Biotage pre-packed silica gel column eluting with 7:3 methylene chloride:methanol to afford the title compound. MS (DCI) m/z 192 (M+H)+.

後処理

  1. temperatureThe mixture was cooled
  2. filtrationthe catalyst filtered off
  3. washwashed with hot ethanol
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe residue purified by normal phase HPLC on a Biotage pre-packed silica gel column
  6. washeluting with 7:3 methylene chloride

出典と根拠

ORDレコード
ord-7d9a796838974b968ebe8ead506b1133
出典データセット
uspto-grants-2015_09
特許番号
US09133145B2

反応ノート

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