Ammonia → HCID 16100402, compound

HRID 1361435Notes

Reaction equation

HRID 1361435 reaction equation
[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>[Ni].C(O)C>[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

Participants

5

Reactant 2

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

Product 1

HCID 16100402HCID 16100402, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

(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)+.

Workup

  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

Sources & evidence

ORD record
ord-79e7f843dcff4a3099fd86bf14da12c5
Source dataset
uspto-grants-2011_02
Patent number
US07880001B2

Reaction notes

Loading…