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

HRID 1288032Notes

Reaction equation

HRID 1288032 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-a03961ce93cd4780a4d7fa4d01184531
Source dataset
uspto-grants-1976_10
Patent number
US03987053

Reaction notes

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