Propylamine → 3-Nitro-4-(propylamino)benzonitrile

HRID 895510Notes

Reaction equation

HRID 895510 reaction equation
Cl[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]([NH2:16])[CH2:14][CH3:15]>C(O)(C)C>[CH2:13]([NH:16][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 13655Benzonitrile, 4-chloro-3-nitro-

Product 1

HCID 230793333-Nitro-4-(propylamino)benzonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirring suspension of 4-chloro-3-nitrobenzonitrile (7.30 g, 40 mmol) in isopropanol (30 mL) is added n-propylamine (9.87 mL, 120 mmol). The mixture is stirred at room temperature for 5 h, and the solid is then collected by filtration to give 4-n-propylamino-3-nitrobenzonitrile as a yellow solid. 1H NMR (CDCl3) δ 8.51 (1H, q), 8.42(1H, br s), 7.60(1H, m), 6.91(1H, d), 3.33(2H, q), 1.84-1.74(2H, m), 1.07(3H, t). LRMS 206.3 (MH+).

Workup

  1. filtrationthe solid is then collected by filtration

Sources & evidence

ORD record
ord-76aed56e07864daf85efb0da7f6db112
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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