Water → Ethyl 3-amino-4-[(3-cyanophenylamino)methyl]benzoate

HRID 219428Notes

Reaction equation

HRID 219428 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][CH2:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][C:12]=2[N+:22]([O-])=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].O.[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:22][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][C:11]=1[CH2:10][NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 18001123Ethyl 4-[(3-cyanophenylamino)methyl]-3-nitrobenzoate

Product 1

HCID 18001133Ethyl 3-amino-4-[(3-cyanophenylamino)methyl]benzoateYield 108.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Ethyl 4-[(3-cyanophenylamino)methyl]-3-nitrobenzoate (5.79 g) was dissolved in 50 ml of ethanol, then 50 ml of purified water, 0.96 g of ammonium chloride and 4.97 g of iron powder were added and the mixture was refluxed under heating for 40 minutes. The reaction solution was filtered through Celite and concentrated in vacuo. Ethyl acetate was added to the resulting residue. The mixture was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, concentrated in vacuo and dried to give 5.71 g of ethyl 3-amino-4-[(3-cyanophenylamino)methyl]benzoate.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 40 minutes
  3. filtrationThe reaction solution was filtered through Celite
  4. concentrationconcentrated in vacuo
  5. additionEthyl acetate was added to the resulting residue
  6. washThe mixture was washed with a saturated aqueous solution of sodium bicarbonate
  7. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customdried

Sources & evidence

ORD record
ord-6e9dc294872c4f2dba6976cd0ea7581f
Source dataset
uspto-grants-2012_06
Patent number
USRE043481E1

Reaction notes

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