Ammonium Hydroxide → 3-(Aminomethyl)-5-fluorobenzonitrile

HRID 572568Notes

Reaction equation

HRID 572568 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:6]#[N:7].[OH-].[NH4+:13]>C1COCC1>[NH2:13][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:6]#[N:7]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 666526293-(Bromomethyl)-5-fluorobenzonitrile2×

Product 1

HCID 666526093-(Aminomethyl)-5-fluorobenzonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To 3-(bromomethyl)-5-fluorobenzonitrile (Intermediate 14, step 1, 10 g, 0.47 mol) in THF (50 mL) was added ammonium hydroxide solution 25% (2.0 L). The resulting mixture was stirred for 2 h at 85° C. It was then cooled down to RT and extracted with dichloromethane. The organic layer was washed with water, brine, dried and concentrated, affording the title compound as a slight yellow liquid (5 g, 71%). 1H NMR (DMSO-d6, 400 MHz): δ 7.6 (d, J=6.6 Hz, 1H), 7.57 (t, J=0.6 Hz, 1H), 7.55 (s, 1H), 3.74 (d, 2H), 1.97 (s, 2H). LC/MS (Method A) 151.0 (M+H)+. HPLC (Method A) Rt: 0.88 min (Purity 98%).

Workup

  1. temperatureIt was then cooled down to RT
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-891d64a1d85843d78e6900ed3744bc3a
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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