Imidazole → methyl 6-(1H-imidazol-1-yl)nicotinate

HRID 1031423Notes

Reaction equation

HRID 1031423 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.[Na].[H-].[Na+].N1C=CN=C1>CN(C=O)C>[N:12]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 57373095Imidazole sodium

Product 1

HCID 4315458methyl 6-(1H-imidazol-1-yl)nicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A solution of the methyl ester obtained in Step 1. above (16.29 g) in DMF is added dropwise to a DMF suspension of sodium imidazole [prepared from NaH (4.19 g) and imidazole 6.49 g)] at RT. The reaction mixture is heated to 120° C. for nineteen hours. The cooled reaction mixture is partitioned between water and chloroform, the organic layer separated, washed with water, dried over Na2SO4, filtered, evaporated, and residual DMF removed under high vacuum yielding the desired product as a tan solid which is recrystalized from methanol (M.P. 183°-184.5° C.) before use in the next step.

Workup

  1. customThe cooled reaction mixture
  2. customis partitioned between water and chloroform
  3. customthe organic layer separated
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customresidual DMF removed under high vacuum

Sources & evidence

ORD record
ord-7a26954fa51e47a0b75f6a3409012ef8
Source dataset
uspto-grants-1990_09
Patent number
US04954494

Reaction notes

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