Acetic Acid → 4-(Pyridin-3-yl)-1,2-oxazol-5-amine

HRID 1604398Notes

Reaction equation

HRID 1604398 reaction equation
CN(C)[CH:3]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[C:4]#[N:5].Cl.[NH2:14]O.[C:16]([OH:19])(=O)C>>[NH2:14][C:16]1[O:19][N:5]=[CH:4][C:3]=1[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 19603622HCID 19603622, compound

Product 1

HCID 167406694-(Pyridin-3-yl)-1,2-oxazol-5-amine

Conditions

Temperature
100 °C

Procedure

To a solution of α-(dimethylamino)-α-(3-pyridyl)acetonitrile (5.19 g, 30 mmol) in acetic acid (40 ml) was added hydroxylamine hydrochloride (2.8 g, 40 mmol). The reaction mixture was stirred at 100° C. for 1 hour, cooled to room temperature and concentrated in vacuo. Water (50 ml) was added and the reaction mixture neutralized with solid potassium carbonate. The precipitated compound was filtered washed with water and dried giving the title compound in 4.2 g yield.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionWater (50 ml) was added
  4. filtrationThe precipitated compound was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-44726756555341708a135445766640bd
Source dataset
uspto-grants-1999_11
Patent number
US05994373

Reaction notes

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