Ammonia → HCID 19597971, compound

HRID 611628Notes

Reaction equation

HRID 611628 reaction equation
[C:1]1([CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([F:20])[F:19])[C:12]#[N:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N.[H][H]>[Ni].CO>[C:1]1([CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([F:19])[F:20])[CH2:12][NH2:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 19597903HCID 19597903, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19597971HCID 19597971, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(naphth-1-yl)-7,7-difluoroheptanenitrile (413 mg, 1.51 mmol), Raney nickel (413 mg) and ammonia (0.9 g) in methanol (20 ml) was hydrogenated under 340 kPa (50 psi) hydrogen overnight at room temperature. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (40 ml) and the ethyl acetate extract was washed with brine (30 ml), dried (sodium sulfate) and concentrated in vacuo. The residue (400 mg) was purified by column chromatography on silica gel (100 g), eluting with 85:15 ethyl acetate/methanol to yield the title compound as an oil (321 mg, 77% yield). 1H NMR (300 MHz, CDCl3) δ1.35 (c, 6H), 1.78 (c, 4H), 3.08 (c, 2H), 3.61 (c, 1H), 5.52, 5.71, 5.9 (3t, total 1H), 7.37 (d, 1H), 7.5 (m, 3H), 7.75 (d, 1H), 7.88 (d, 1H), 8.16 (d, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate (50 ml) and water (40 ml)
  4. extractionthe ethyl acetate extract
  5. washwas washed with brine (30 ml)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customThe residue (400 mg) was purified by column chromatography on silica gel (100 g)
  9. washeluting with 85:15 ethyl acetate/methanol

Sources & evidence

ORD record
ord-e9b00d0b0f29479f8eb502c54e15e398
Source dataset
uspto-grants-1999_12
Patent number
US06001860

Reaction notes

Loading…