Aniline → 2-Aminophenyl-4-nitro-benzonitrile

HRID 1609855

Reaction equation

HRID 1609855 reaction equation
Cl[C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN1CCCC1=O.C(N(C(C)C)CC)(C)C>CCOC(C)=O>[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 6115AnilineHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 1414012-Chloro-4-nitrobenzonitrile

Product 1

HCID 179479572-Aminophenyl-4-nitro-benzonitrileYield 88.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-4-nitro-benzonitrile (Aldrich) (3.64 g, 20 mmol), aniline (2 mL, 22 mmol), 1-methyl-2-pyrollidinone (10 mL) and diisopropylethylamine (4 mL) were combined and heated to 120° under Ar for 18 h, cooler poured into EtOAc (150 mL), washed with H20 (3×50 mL) and satd aq NaCl (50 mL), dried (Na2SO4), concentrated, and the residue was triturated with hexane, filtered and the solid was washed with hexane and dried in vacuo to afford 4.23 g (88%) of the title compound as a light green solid. 1H NMR (400) MHz, δ: 8.45 (finely split doublet, 1), 8.19 (dd, 1), 7.48 (m,3), 7.28 (d,2), 7.06 (d,1), 6.96 (br s,1).

Workup

  1. temperatureheated to 120° under Ar for 18 h
  2. washwashed with H20 (3×50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue was triturated with hexane
  6. filtrationfiltered
  7. washthe solid was washed with hexane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-5a79adfa8994446aaeb07317d99fe9e9
Source dataset
uspto-grants-2006_01
Patent number
US06982270B1

Linked notes

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