Ethylamine → 4-(Ethylamino)-3-nitrobenzonitrile

HRID 600819Notes

Reaction equation

HRID 600819 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([NH2:15])[CH3:14]>C1COCC1>[CH2:13]([NH:15][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[CH3:14]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 31180704-(Ethylamino)-3-nitrobenzonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-fluoro-3-nitrobenzonitrile (5.0 g, 30 mmol) in THF (15 mL, anhyd) was added a solution of ethylamine (2.0 M, 23 mL, 46 mmol) in THF. After stirring 16 h, precipitated solids were collected by filtration, triturated with a mixture of THF-hexanes (1:1, 50 mL), filtered again and dried under vacuum to give 4-ethylamino-3-nitrobenzonitrile (4.7 g, 82%) as a yellow solid. 1H-NMR (CDCl3): δ 8.51 (1H, d), 8.34 (1H, br s), 7.62 (1H, dd), 6.93 (1H, d), 3.44 (2H, m), 1.42 (3H, t).

Workup

  1. customprecipitated solids
  2. filtrationwere collected by filtration
  3. customtriturated with a mixture of THF-hexanes (1:1, 50 mL)
  4. filtrationfiltered again
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4e650fd3bd4d4a5c94d653e387ccea06
Source dataset
uspto-grants-2011_03
Patent number
US07902237B2

Reaction notes

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