Hydrochloric Acid → 4-Imidazol-1-yl-2-methyl-6-nitro-phenylamine

HRID 1793694Notes

Reaction equation

HRID 1793694 reaction equation
[N:1]1([C:6]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([NH:15]C(=O)C)=[C:8]([CH3:19])[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.C([O-])(O)=O.[Na+]>C(O)C>[N:1]1([C:6]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([NH2:15])=[C:8]([CH3:19])[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22021016N-(4-Imidazol-1-yl-2-methyl-6-nitro-phenyl)-acetamide

Product 1

HCID 220210264-Imidazol-1-yl-2-methyl-6-nitro-phenylamineYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of N-(4-imidazol-1-yl-2-methyl-6-nitro-phenyl)-acetamide (279 mg, 1.07 mmol) in ethanol (3 mL) was added 2 N HCl (2 mL). The reaction mixture was heated to reflux for 14 h, cooled to room temperature, and neutralized with saturated NaHCO3. The resulting bright orange solid was filtered and dried under vacuum. The title compound (179 mg, 76%) was obtained as an orange solid. 1H NMR (300 MHz, CD3OD) δ 8.78 (1H, s), 8.24 (1H, s), 7.78 (1H, s), 7.64 (1H, s), 7.46 (1H, s), 2.36 (3H, s).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 14 h
  3. filtrationThe resulting bright orange solid was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-16361839952e4c2f9aaa29ec6e0c26d9
Source dataset
uspto-grants-2006_07
Patent number
US07081454B2

Reaction notes

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