Hydrochloric Acid → 4-Nitro-3-phenethylaminobenzonitrile

HRID 1858019Notes

Reaction equation

HRID 1858019 reaction equation
CO[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:6]#[N:7].Cl.[CH2:15]([NH2:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+].Cl>CS(C)=O>[N+:11]([C:10]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH:23][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 90752-Phenylethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 108992273-Methoxy-4-nitrobenzonitrile

Product 1

HCID 221254994-Nitro-3-phenethylaminobenzonitrileYield 51.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture comprising 3-methoxy-4-nitrobenzonitrile (1 g, 5.6 mmol), phenethylamine hydrochloride (1.8 g, 11.2 mmol), 50% sodium hydroxide (0.9 g, 11.2 mmol) and DMSO (3 mL) was heated at 100° C. for 3.5 hours, cooled and poured into a solution of 1N hydrochloric acid (200 mL, 0° C.). The mixture was stirred for 20 minutes to give a precipitate. The precipitate was collected and recrystallized from hot ethanol to provide 4-nitro-3-phenethylaminobenzonitrile (0.78 g, 2.9 mmol) as orange crystals. MS (CI), Calculated for C15H13N3O2, 267.3, Found (MH+): 282. A mixture comprising 4-nitro-3-phenethylaminobenzonitrile (0.75 g, 2.8 mmol), palladium on carbon (100 mg) and 1:1 methanol/THF (100 mL) was hydrogenated under 1 atm for 3 hours, filtered and concentrated under reduced pressure to provide 4-amino-3-phenethylaminobenzonitrile (0.68 g, 2.8 mmol) as a tan solid.

Workup

  1. temperaturecooled
  2. customto give a precipitate
  3. customThe precipitate was collected
  4. customrecrystallized from hot ethanol

Sources & evidence

ORD record
ord-f5f739ff31d642b2becee17c59ee6ef3
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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