Nitrogen → 7-Methoxy-1-naphthaleneethanamine

HRID 572699Notes

Reaction equation

HRID 572699 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]#[N:15])=[CH:5][CH:4]=1.O.N.N#N>[Ni].C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH2:15])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 112640682-(7-Methoxynaphthalen-1-yl)acetonitrileHCID 12896473Azane;hydrate

Product 1

HCID 110526677-Methoxy-1-naphthaleneethanamineYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

56 g 7-methoxy-1-naphthaleneacetonitrile, 120 ml ammonia water, 332 ml 95% ethanol, 20 g Raney-Ni were added into autoclave. H2 was introduced after vacuuming it. The operation was repeated for 3 times. The reaction was stirred for 12 hours while H2 was introduced and the condition of 300 atm and 60° C. was maintained. After completion of the reaction, the reaction was kept overnight at room temperature. On the next day, it was vacuumed and N2 gas was introduced. The autoclave was opened up, and the reaction solution was filtered to remove the catalyst. The filtrate was vacuum evaporated until dry to obtain 56 g light green oil. The content is measured as 96.95% by HPLC, and the yield is 95%.

Workup

  1. additionH2 was introduced
  2. additionwas introduced
  3. customAfter completion of the reaction
  4. waitthe reaction was kept overnight at room temperature
  5. filtrationthe reaction solution was filtered
  6. customto remove the catalyst
  7. customevaporated
  8. customuntil dry

Sources & evidence

ORD record
ord-b5a5db2d1d394bd89e4740104ffa279c
Source dataset
uspto-grants-2015_05
Patent number
US09029420B2

Reaction notes

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