Ethylamine → 6-Chloro-2-ethylamino-3-nitro-benzonitrile

HRID 2246899Notes

Reaction equation

HRID 2246899 reaction equation
[CH2:1]([NH2:3])[CH3:2].Cl[C:5]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9]([Cl:16])[C:6]=1[C:7]#[N:8]>C1COCC1.CCOC(C)=O>[Cl:16][C:9]1[C:6]([C:7]#[N:8])=[C:5]([NH:3][CH2:1][CH3:2])[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 6341EthylamineHCID 44619322,6-Dichloro-3-nitrobenzonitrile

Product 1

HCID 109221976-Chloro-2-ethylamino-3-nitro-benzonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethylamine in THF (2 M, 13.8 mL, 27.6 mmol) was added slowly to a solution of 2,6-dichloro-3-nitrobenzonitrile (3.0 g, 13.8 mmol) in THF (30 mL) at −5° C. After 1.5 h, the solution was diluted with EtOAc (150 mL) and washed with 0.5 N HCl and brine. Organics were dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography (8:1:1 hexanes/CHCl3/EtOAc) gave 2.57 g (82%) of the title compound as an orange solid. 1H NMR (400 MHz, CDCl3): δ 8.51 (br s, 1H), 8.30 (d, 1H, J=8.8 Hz), 6.78 (d, 1H, J=8.4 Hz), 3.89-3.97 (m, 2H), 1.41 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C9H8N3O2Cl, 226, 228; found 226, 228.

Workup

  1. washwashed with 0.5 N HCl and brine
  2. dry with materialOrganics were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by silica gel chromatography (8:1:1 hexanes/CHCl3/EtOAc)

Sources & evidence

ORD record
ord-c0acf18d3d994971b269a07f540a4026
Source dataset
uspto-grants-2010_03
Patent number
US07687638B2

Reaction notes

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