Ammonia → 4-(Aminomethyl)-2-methoxybenzonitrile
Reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH3:12])[CH:4]=1.CO.[NH3:15].N.CO>C(Cl)Cl>[NH2:15][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH3:12])[CH:4]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2.5 g of the bromide (b) were introduced into 10 ml of MeOH, and NH3 was passed in during dropwise addition of 38 ml of conc. ammonia/MeOH 1:1. After 2 h, the solvent was stripped off, the product was taken up in DCM and washed with water, and the organic phase was dried over Na2SO4. The product was precipitated as hydrochloride with ethereal HCl. 1H-NMR (DMSO-d6, δ in ppm): 8.6 (broad signal, NH3+), 7.79 (1H), 7.55 (1H), 7.20 (1H), 4.10 (s, 2H), 3.93 (s, 3H)
Workup
- washwashed with water
- dry with materialthe organic phase was dried over Na2SO4
- customThe product was precipitated as hydrochloride with ethereal HCl
Sources & evidence
- ORD record
- ord-9d67b28124344561a17a4f48759d32e0
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06444817B1
Reaction notes
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