Ammonia → 4-(Aminomethyl)-2-methoxybenzonitrile

HRID 1278926Notes

Reaction equation

HRID 1278926 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]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 21705897Ammonia methanolHCID 219850074-(Bromomethyl)-2-methoxybenzonitrile

Product 1

HCID 224761464-(Aminomethyl)-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. washwashed with water
  2. dry with materialthe organic phase was dried over Na2SO4
  3. 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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