2-Methoxybenzaldehyde → Amino(2-methoxyphenyl)acetonitrile

HRID 1089867Notes

Reaction equation

HRID 1089867 reaction equation
[C-:1]#[N:2].[Na+].[Cl-].[NH4+:5].[OH-].[NH4+].[CH:8](=O)[C:9]1[C:10]([O:15][CH3:16])=[CH:11][CH:12]=[CH:13][CH:14]=1.C([O-])(=O)C(C(C([O-])=O)O)O>O.C(OCC)(=O)C.CO>[NH2:5][CH:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])[C:1]#[N:2]

Participants

9

Reactant 5

HCID 86582-MethoxybenzaldehydeHCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 38061142,3-Dihydroxybutanedioate

Product 1

HCID 13401092Amino(2-methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 50.0 g (1.0 mol) of sodium cyanide, 53.5 g (1.0 mol) of ammonium chloride, and 60 mL of concentrated ammonium hydroxide in 400 mL of water was added 125 g (0.92 mol) of o-anisaldehyde in 400 aromatic C-C); of dry methanol. After the mixture was stirred for 3 h at 23° C., the methanol was removed under reduced pressure, and the residual solution containing the crude product was diluted with 500 mL of water and extracted with methylene chloride (2×400 mL), dried over sodium sulfate, and filtered; the solvent was subsequently removed under vacuum to give an orange oil. By means of column chromatography on silica gel using ethyl acetate as the eluent, the o-amino nitrile compound (A) was separated from the starting material and the side products; IR (neat) 2240 (w, --C≡N), 1600, 1500 cm1 (s, aromatic C=C); NMR (CDCL3) 1.03 (2 H, s, NH2), 3.90 (3 H, s, OCH3), 5.05 (1 H, s, CH), 7.15 (4 H m, ArH). The α-amino nitrile (yellow oil) was unstable as a free base; therefore it was either used immediately for the next reaction or converted to the tartarate salt.

Workup

  1. customthe methanol was removed under reduced pressure
  2. additionthe residual solution containing the crude product
  3. additionwas diluted with 500 mL of water
  4. extractionextracted with methylene chloride (2×400 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was subsequently removed under vacuum
  8. customto give an orange oil
  9. customthe o-amino nitrile compound (A) was separated from the starting material
  10. customtherefore it was either used immediately for the next reaction

Sources & evidence

ORD record
ord-0472222a5f194783bdc2c30d325cf016
Source dataset
uspto-grants-1992_01
Patent number
US05079346

Reaction notes

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