Sodium Chloride → 3-Amino-4-{[(2,4-dimethoxyphenyl)methyl]amino}benzonitrile

HRID 605855Notes

Reaction equation

HRID 605855 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[N+:15]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Na+].[Cl-]>C1COCC1.O.CCOC(C)=O.CO>[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH2:15]

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 669708084-(2,4-Dimethoxybenzylamino)-3-nitrobenzonitrile

Product 1

HCID 566052433-Amino-4-{[(2,4-dimethoxyphenyl)methyl]amino}benzonitrileYield 105.5%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(2,4-dimethoxybenzylamino)-3-nitrobenzonitrile (4.54 g) in THF (400 mL) was treated with a solution of sodium hydrosulfite (20 g) and sodium bicarbonate (10 g) in distilled water (350 mL). Enough methanol was immediately added (50 mL) to maintain a homogeneous solution. After 15 minutes, EtOAc (500 mL) and saturated aqueous NaCl (500 mL) were added and the organic layer was separated. The aqueous layer was extracted again with 400 mL EtOAc. The combined organic layers were washed with saturated aqueous NaCl (500 mL) and separated. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to provide 4.33 g of the title compound.

Workup

  1. temperatureto maintain a homogeneous solution
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted again with 400 mL EtOAc
  4. washThe combined organic layers were washed with saturated aqueous NaCl (500 mL)
  5. customseparated
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b95826a2df044f699184e2cc39007d0
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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