Benzylamine → Ethyl 3-(benzylamino)-4-nitrobenzoate

HRID 1258934Notes

Reaction equation

HRID 1258934 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([NH:8][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 45036938Ethyl 3-Fluoro-4-nitrobenzoate

Product 1

HCID 58213841Ethyl 3-(benzylamino)-4-nitrobenzoateYield 107.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzylamine (0.77 mL, 7.0 mmol), ethyl 3-fluoro-4-nitrobenzoate (1.0 g, 4.7 mmol) and TEA (2 mL) was heated in DMF (10 mL) for 18 hr at 70° C. The solution was cooled to room temperature, diluted with ethyl acetate (200 mL) and washed with H2O (2×100 mL) then 1N HCl (2×100 mL). The organic layer was dried (MgSO4), filtered and then concentrated to provide 1.52 g (˜100%) of crude ethyl 3-(benzylamino)-4-nitrobenzoate as an orange solid. This material was used without further purification.

Workup

  1. washwashed with H2O (2×100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f48122e6a5e148078ec95759b6d4bd28
Source dataset
uspto-grants-2013_06
Patent number
US08466193B2

Reaction notes

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