6-fluoro-2H-chromene-3-carbonitrile → (6-Fluorochroman-3-YL)methanamine

HRID 536468Notes

Reaction equation

HRID 536468 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][C:6]([C:12]#[N:13])=[CH:5]2>N.CO.[Ni]>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH:6]([CH2:12][NH2:13])[CH2:5]2

Participants

5

Reactant 1

HCID 150274626-fluoro-2H-chromene-3-carbonitrile

Product 1

HCID 15027463(6-Fluorochroman-3-YL)methanamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of Example 28A (780 mg, 4.45 mmol) in 7M NH3 in MeOH (5.00 mL) was added to Ra—Ni 2800 water slurry (1.56 g, 26.6 mmol) in a 50 mL pressure bottle. The reaction mixture was and stirred for 10 hours at 30 psi at ambient temperature. After 3 hours, the solution was filtered and concentrated. The resulting residue was purified by silica gel chromatography (gradient elution: 1-15% MeOH/CH2Cl2 with 1% NH4OH) to provide the title compound. MS (DCI+) m/z 182 (M+H)+.

Workup

  1. waitAfter 3 hours
  2. filtrationthe solution was filtered
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel chromatography (gradient elution: 1-15% MeOH/CH2Cl2 with 1% NH4OH)

Sources & evidence

ORD record
ord-7d72175578584c33a4f8163f0c8120b5
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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