Potassium Carbonate → 3-(Cyclopropylamino)-4-nitrobenzonitrile

HRID 1048965Notes

Reaction equation

HRID 1048965 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].C([O-])([O-])=O.[K+].[K+].[CH:19]1([NH2:22])[CH2:21][CH2:20]1>C(Cl)Cl.O>[CH:19]1([NH:22][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[N+:10]([O-:12])=[O:11])[C:5]#[N:6])[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 27833993-Fluoro-4-nitrobenzonitrile

Product 1

HCID 666833633-(Cyclopropylamino)-4-nitrobenzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-fluoro-4-nitrobenzonitrile (2.0 g, 0.012 mol) in DCM (20 ml), was added K2CO3 (3.3 g, 0.024 mol) and cyclopropyl amine (6.7 ml, 0.096 mol) and the resulting solution was continued to stir at room temperature for 3 h. The reaction was diluted with cold water and extracted with dichloromethane (3×100 ml). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under vacuum to afford the title compound 3-(cyclopropylamino)-4-nitrobenzonitrile as a yellow solid. 1H NMR (400 MHz, CDCl3), δ: 8.24-8.22 (d, J=8.8 Hz, 1H), 8.07 (bs, 1H), 7.64 (s, 1H), 6.94-6.92 (d, J=8.8 Hz, 1H), 2.59-2.58 (m, 1H), 1.25-0.97 (m, 2H), 0.71-0.58 (m, 2H). MS (M+1): 204.

Workup

  1. extractionextracted with dichloromethane (3×100 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5819e3210cd14e3cab17bb8667f663dc
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

Loading…