Sulfuric Acid → 4-(Aminomethyl)-N-(2-aminophenyl)benzamide

HRID 1509991Notes

Reaction equation

HRID 1509991 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1.S(=O)(=O)(O)O.[H][H]>CO.[Pd]>[NH2:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH2:1])=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 16790771HCID 16790771, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 588172504-(Aminomethyl)-N-(2-aminophenyl)benzamideYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(2-aminophenyl)-4-cyanobenzamide (237 mg, 1 mmol) in methanol (40 ml) was added sulfuric acid (196 mg, 1 mmol) and 5% palladium on charcoal (0.20 g). The mixture was stirred under an atmosphere of hydrogen at room temperature until hydrogen uptake ceased. The mixture was filtered through celite, and the filtrate was neutralized with 1 N NaOH solution in methanol (2 ml). The resulting mixture was filtered, and the filtrate was evaporated under vacuum to give the title compound (232 mg, 96% yield) as a grey solid. LC-MS (m/z) 242 (M+1).

Workup

  1. filtrationThe mixture was filtered through celite
  2. filtrationThe resulting mixture was filtered
  3. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-062ce395abd7475d833a828b99b86ee9
Source dataset
uspto-grants-2012_07
Patent number
US08211901B2

Reaction notes

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