1-Methyl-2-imidazolecarboxaldehyde → HCID 136239730, compound

HRID 1650680Notes

Reaction equation

HRID 1650680 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.Cl.[NH2:10][OH:11].C(=O)(O)[O-].[Na+]>C(O)C>[OH:11][N:10]=[CH:7][C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 136239730HCID 136239730, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture consisting of 118.4 grams of 1-methylimidazole-2-carboxaldehyde, 82.5 grams of hydroxylamine hydrochloride, 113.9 grams of sodium bicarbonate and 1300 ml of absolute ethanol was heated under reflux for 2 hours and then filtered while still hot. The filtrate was concentrated to give a colorless residue which was recrystallized from 2-propanol to give 75 grams of 2-(hydroxyimino)methyl-1-methylimidazole as colorless crystals melting at 170°-172° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. filtrationfiltered while still hot
  4. concentrationThe filtrate was concentrated
  5. customto give a colorless residue which
  6. customwas recrystallized from 2-propanol

Sources & evidence

ORD record
ord-ae75eeaba8e84f7fbd80f63bfa788b41
Source dataset
uspto-grants-1990_05
Patent number
US04925856

Reaction notes

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