Ammonia → (7-Fluoroquinolin-6-yl)methanamine

HRID 449252Notes

Reaction equation

HRID 449252 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[C:12]#[N:13].N>[Ni].CO>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][NH2:13]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 593419177-Fluoroquinoline-6-carbonitrile

Product 1

HCID 52987914(7-Fluoroquinolin-6-yl)methanamineYield 78.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To 7-fluoroquinoline-6-carbonitrile (1.00 g, 5.813 mmol), methanol saturated with ammonia (13.5 ml) and Raney-Ni (1.27 g) were added and hydrogenated at 50-60 psi for 4 h. The reaction mixture was filtered and concentrated to afford the title compound as a brown oil (0.80 g, 78%). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.85 (d, J=2.3 Hz, 1H), 8.35 (d, J=8.0 Hz, 1H), 8.06 (d, J=9.5 Hz, 1H), 7.68 (d, J=11.8 Hz, 1H), 7.49 (t, J=3.8 Hz, 1H), 3.92 (s, 2H), 1.90 (br s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-52be0470c5254ace8c81ee3034d96550
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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