Imidazole → Methyl 5-amino-6-(1H-imidazol-1-yl)nicotinate

HRID 69615

Reaction equation

HRID 69615 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>[NH2:12][C:11]1[C:2]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 795ImidazoleHCID 346961Methyl 6-chloro-5-nitronicotinate

Product 1

HCID 58324506Methyl 5-amino-6-(1H-imidazol-1-yl)nicotinate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 11430Potassium CarbonateSolvent

Procedure

Methyl 6-chloro-5-nitronicotinate (2.17 g, 10.0 mmol) was dissolved in ethyl acetate (55 mL) and imidazole (4.09 g, 60 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and treated with SnCl2-2H2O (13.5 g, 60.0 mmol). It was heated to 70° C. for 2 h, diluted with potassium carbonate (sat. aq.) and extracted with ethyl acetate (5×20 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a crude yellow solid, which was used in the next step without further purification. [M+H] calc'd for C10H10N4O2, 219; found, 219.

Workup

  1. temperatureIt was heated to 70° C. for 2 h
  2. extractionextracted with ethyl acetate (5×20 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82316eaf647e4e129a11cd1ae2be3002
Source dataset
uspto-grants-2014_09
Patent number
US08822470B2

Linked notes

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