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

HRID 1767005Notes

Reaction equation

HRID 1767005 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-52e30996165b44e587a92eae26b3002f
Source dataset
uspto-grants-2007_06
Patent number
US07232826B2

Reaction notes

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