Ammonia → HCID 21824590, compound

HRID 462106Notes

Reaction equation

HRID 462106 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[C:6]([CH2:10][C:11]#N)[C:5]([CH2:13][C:14]#[N:15])=[CH:4][C:3]=2[O:2]1.N>[Ni]>[CH2:1]1[O:2][C:3]2[C:8](=[CH:7][C:6]3[CH2:10][CH2:11][NH:15][CH2:14][CH2:13][C:5]=3[CH:4]=2)[O:9]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14620574HCID 14620574, compound

Product 1

HCID 21824590HCID 21824590, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

119 g. (0.595 moles) of 4,5-methylenedioxy-1,2-benzenediacetonitrile was hydrogenated in 2.4 l. of ammonia-saturated ethanol at an initial pressure of 1,000 PSI and 100° C in the presence of 24 g of Raney nickel for 4 to 5 hours. The cooled autoclave contents were filtered to remove the nickel, the catalyst washed with 500 ml of hot ethanol, and the filtrate distilled at reduced pressure, leaving 120 g of dark gray oil. This oil was distilled in vacuo using a Claisen still head and several fractions were collected. The low boiling fractions contained the desired produ ct which upon purification yielded the above-named product, m.p. 82°-84°.

Workup

  1. filtrationThe cooled autoclave contents were filtered
  2. customto remove the nickel
  3. washthe catalyst washed with 500 ml of hot ethanol
  4. distillationthe filtrate distilled at reduced pressure

Sources & evidence

ORD record
ord-4cf2d5b72abc48ac82ffdfb5f8016d0f
Source dataset
uspto-grants-1977_12
Patent number
US04065473

Reaction notes

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