Diethyl Ether → HCID 22063668, compound

HRID 1828542

Reaction equation

[NH2:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.[N:13]([O-])=O.[Na+].C(OCC)C.[F:22][B-:23]([F:26])([F:25])[F:24].[H+]>>[F:22][B-:23]([F:26])([F:25])[F:24].[C:9]([NH:8][C:5]1[N:6]=[CH:7][C:2]([N+:1]#[N:13])=[C:3]([CH3:12])[CH:4]=1)(=[O:11])[CH3:10]

Participants

Reactant 4

HCID 3283Diethyl Ether

HCID 28118Tetrafluoroboric acid

HCID 22063573N-(5-Amino-4-methylpyridin-2-yl)acetamide2×

HCID 23668193Sodium Nitrite

Product 1

HCID 22063668HCID 22063668, compound

Conditions

Temperature: -10 °C

Procedure

The N1-(5-amino-4-methyl-2-pyridyl)acetamide (8.00 g, 48.4 mmol) obtained in (B) was dissolved in tetrafluoroboric acid (160 ml) and slowly added dropwise with an aqueous solution (40 ml) of sodium nitrite (3.51 g, 50.8 mmol) at −20° C. under nitrogen atmosphere. The reaction mixture was further stirred at −10° C. for 1 hour and added with diethyl ether (800 ml), and the deposited white solid was collected by filtration and washed with diethyl ether to obtain the title compound (14.7 g, quantitative).

Workup

filtrationthe deposited white solid was collected by filtration
washwashed with diethyl ether

Sources & evidence

ORD record: ord-cbb21bec42474f60a019da7ee26d175a
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Linked notes

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