Hydroxyamine hydrochloride → HCID 178498809, compound

HRID 2381954Notes

Reaction equation

HRID 2381954 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)=[O:4].Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([C:11](=[NH:12])[NH:14][OH:15])=[N:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 23625856HCID 23625856, compound

Product 1

HCID 178498809HCID 178498809, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-cyano-pyrimidine-5-carboxylic acid methyl ester 3 (1 g, 6.13 mmol) in MeOH (20 mL) at rt is added hydroxylamine hydrochloride (0.64 g, 9.2 mmol) and sodium acetate (0.76 g, 9.2 mmol). The resulting mixture is heated to reflux for 2 hours. The mixture is cooled to rt and concentrated in vacuo. Water (30 mL) is added to the residue, and the solid is filtered, and washed with water twice. The solid is dried in vacuum oven overnight to afford 2-(N-hydroxycarbamimidoyl)-pyrimidine-5-carboxylic acid methyl ester (1.09 g, 91%) as a solid. MS: 197 (M+H).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated in vacuo
  4. additionWater (30 mL) is added to the residue
  5. filtrationthe solid is filtered
  6. washwashed with water twice
  7. customThe solid is dried in vacuum oven overnight

Sources & evidence

ORD record
ord-829731bc66c9488b8521b8efab0e9c59
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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