Hydroxyamine hydrochloride → 3-(Pyridin-4-yl)-1,2-oxazol-5-amine

HRID 491531Notes

Reaction equation

HRID 491531 reaction equation
O=[C:2]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].Cl.[NH2:13][OH:14]>C(O)C>[N:9]1[CH:10]=[CH:11][C:6]([C:2]2[CH:3]=[C:4]([NH2:5])[O:14][N:13]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 157315353-Oxo-3-(pyridin-4-yl)propanenitrile

Product 1

HCID 127178543-(Pyridin-4-yl)-1,2-oxazol-5-amineYield 68.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To 3-oxo-3-pyridin-4-yl-propionitrile (2.0 g, 13.7 mmol) in 20 mL of ethanol was added hydroxylamine hydrochloride (0.75 g, 10.8 mmol) and the resulting solution was heated at 70° C. overnight. The resulting white precipitate was collected and the solution was concentrated and dried in vacuum to afford the title compound (1.2 g, 54%) as a yellow solid. FIA MS: MH+162.2, M−160.0.

Workup

  1. customThe resulting white precipitate was collected
  2. concentrationthe solution was concentrated
  3. customdried in vacuum

Sources & evidence

ORD record
ord-17cb97e1e8d6499e96b5cd3e3bd0b106
Source dataset
uspto-grants-2009_05
Patent number
US07531556B2

Reaction notes

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