Hydrochloric Acid → 1-Methyl-2-nitro-1H-imidazole-5-methanol

HRID 1075968Notes

Reaction equation

HRID 1075968 reaction equation
[C:1]([C:6]1[N:10]([CH3:11])[C:9]([N+:12]([O-:14])=[O:13])=[N:8][CH:7]=1)(OCC)=[O:2].[Li+].[BH4-].Cl>O1CCCC1>[CH3:11][N:10]1[C:6]([CH2:1][OH:2])=[CH:7][N:8]=[C:9]1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 329608Ethyl 1-methyl-2-nitro-1H-imidazole-5-carboxylateHCID 4148881Lithium borohydride2×

Product 1

HCID 702921-Methyl-2-nitro-1H-imidazole-5-methanolYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.2 g. of 5-carbethoxy-1-methyl-2-nitroimidazole in 30 ml. of tetrahydrofuran, 0.044 g. of LiBH4 is gradually added under stirring at room temperature. After stirring for 48 hours, the excess of LiBH4 is decomposed with 10% hydrochloric acid, the reaction mixture is filtered and the filtrated is evaporated to dryness under vacuum. The residue is taken up with acetone. Inorganic salts are filtered off and the solution is evaporated. The oily residue is chromatographed through 7 g. of silica gel, by eluting with chloroform containing from 1% to 3% (v/v) of methanol. After concentration of the portions containing the product, 0.052 g. (33%) of 1-methyl-2-nitro-5-hydroxymethylimidazole is obtained.

Workup

  1. stirringAfter stirring for 48 hours
  2. filtrationthe reaction mixture is filtered
  3. customthe filtrated is evaporated to dryness under vacuum
  4. filtrationInorganic salts are filtered off
  5. customthe solution is evaporated
  6. customThe oily residue is chromatographed through 7 g
  7. washof silica gel, by eluting with chloroform containing from 1% to 3% (v/v) of methanol
  8. additionAfter concentration of the portions containing the product, 0.052 g

Sources & evidence

ORD record
ord-fd56b6156a964fb781103f0166a4746f
Source dataset
uspto-grants-1976_05
Patent number
US03954789

Reaction notes

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