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

HRID 1354598Notes

Reaction equation

HRID 1354598 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-4dd78fe4c0504a8fb0de27397c7d29cd
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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