Ammonia → 4-(Aminomethyl)-2-methoxybenzonitrile

HRID 378327Notes

Reaction equation

HRID 378327 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-5a0e744ad4f649a29fca5093a502c2f2
Source dataset
uspto-grants-2000_02
Patent number
US06030972

Reaction notes

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