Water → 5-phenyl-1H-pyrazin-2-one

HRID 1747776

Reaction equation

Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].O.[OH-].[Na+].O=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:12]=O>CO.C(O)(=O)C>[C:14]1([C:11]2[N:2]=[CH:3][C:4](=[O:5])[NH:6][CH:12]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a mixture of glycine amide hydrochloride (0.73 g), methanol (6.0 mL) and water (1.5 mL) were added a 12.5M aqueous sodium hydroxide solution (0.80 mL) and a solution of sodium hydroxide (0.26 g) in methanol (3.0 mL) at −30° C. Then, a solution of oxo(phenyl)acetaldehyde (1.0 g) in methanol (5.0 mL) was added, and the mixture was stirred at −20° C. for 2 hr and at room temperature for 1 hr. The reaction mixture was neutralized with acetic acid, and the resulting solid was collected by filtration and washed with water to give the title compound (0.86 g).

Workup

customat −30° C
filtrationthe resulting solid was collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-fc80dc711ee24038b3fe02f4bade722e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150588B2

Linked notes

Loading…