Sodium Bicarbonate → N1-Benzylbenzene-1,2-diamine

HRID 2229422Notes

Reaction equation

HRID 2229422 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 521800N-benzyl-2-nitroaniline

Product 1

HCID 2735482N1-Benzylbenzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

[N-(2-Nitrophenyl)]-benzylamine (21.9 mmol, 5.0 g) in ethyl acetate (150 ml) is charged with SnCl22H2O (131 mmol, 29.55 g) and is refluxed for 3 hours. The mixture is poured into ice water (100 g), sodium bicarbonate is added to achieve pH 7, and the reaction mixture is extracted with ethyl acetate (3×50 ml). The organic layer is dried with MgSO4, is filtered and evaporated to yield a light sensitive oil, which is used as such in the next step.

Workup

  1. temperatureis refluxed for 3 hours
  2. additionis added
  3. extractionthe reaction mixture is extracted with ethyl acetate (3×50 ml)
  4. dry with materialThe organic layer is dried with MgSO4
  5. filtrationis filtered
  6. customevaporated
  7. customto yield a light sensitive oil, which

Sources & evidence

ORD record
ord-e3723a2a424848e19487f1a02dfa6528
Source dataset
uspto-grants-2002_07
Patent number
US06420410B1

Reaction notes

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