Benzonitrile, 4-chloro-3-nitro- → HCID 54032321, compound

HRID 1419164Notes

Reaction equation

HRID 1419164 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]1.Cl[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27].C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:22]([C:21]1[CH:24]=[CH:25][C:18]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH:11]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]2)=[C:19]([N+:26]([O-:28])=[O:27])[CH:20]=1)#[N:23]

Participants

5

Reactant 3

HCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 517045Sodium AcetateHCID 10262727HCID 10262727, compound

Product 1

HCID 54032321HCID 54032321, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Amino-3-(N-methylpyrrolidin-3-yl)-1H-indole and 4-chloro-3-nitrobenzonitrile were used. Sodium acetate was used as base, acetic acid was used as solvent, and the reaction was heated at reflux for 5 hours. Column chromatography afforded the title compound (16%) as a red amorphous solid: Rf =0.35 in 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide]; 13C NMR (CDCl3) δ 147.4, 137.0, 135.8, 132.1, 131.4, 128.2, 127.8, 122.2, 120.4, 120.3, 118.2, 117.2, 117.1, 112.7, 98.9, 62.7, 56.3, 42.4, 35.0, 32.3; HRMS calculated for C20H19N5O2 361.1541, found 361.1500.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 5 hours

Sources & evidence

ORD record
ord-92a2fe246a3f403ba7974f9ef0c8d294
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

Loading…