Ethyl 3-(benzylamino)-4-nitrobenzoate → Ethyl 4-amino-3-(benzylamino)benzoate

HRID 1258935Notes

Reaction equation

HRID 1258935 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[N+:20]([O-])=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.C(O)(=O)C.[Zn]>[NH2:20][C:19]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]=1[NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 58213841Ethyl 3-(benzylamino)-4-nitrobenzoate

Product 1

HCID 58213838Ethyl 4-amino-3-(benzylamino)benzoateYield 106.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a stirring solution of ethyl 3-(benzylamino)-4-nitrobenzoate (1.52 g, 5 mmol) in ethanol (50 mL) and acetic acid (7 mL) was added zinc dust (2.3 g, 35 mmol). After 1 hr at room temperature, the solids were filtered and the remaining solution was concentrated. The resulting residue was diluted with ethyl acetate (200 mL) and washed with dilute aq. NaHCO3 (1×100 mL), then the organic layer was dried (MgSO4), filtered and then concentrated to provide 1.44 g (˜100%) of crude ethyl 4-amino-3-(benzylamino)benzoate as an orange/brown oil. This material was used without further purification.

Workup

  1. filtrationthe solids were filtered
  2. concentrationthe remaining solution was concentrated
  3. additionThe resulting residue was diluted with ethyl acetate (200 mL)
  4. washwashed with dilute aq. NaHCO3 (1×100 mL)
  5. dry with materialthe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-27c4d0b04c4c493594451cffc98388be
Source dataset
uspto-grants-2013_06
Patent number
US08466193B2

Reaction notes

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