Potassium Carbonate → 2-[(6-amino-2-pyridinyl)methoxyimino]-N'-hydroxy-2-phenylethanimidamide

HRID 2206857Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)\[C:12]#[N:13])[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].C(=O)([O-])[O-].[K+].[K+]>CC(O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)/[C:12](=[N:21]/[OH:22])/[NH2:13])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of (2Z)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)acetonitrile (4 g, 15.85 mmol, 1 eq.) in iPrOH/H2O (10/1, 110 ml) were added hydroxylamine hydrochloride (3.30 g, 47.56 mmol, 3 eq.) and potassium carbonate (6.57 g, 47.56 mmol, 3 eq.). The reaction was heated to 80° C. for 6 h and the solvent was evaporated to ¾th. The residue was extracted with EtOAc (3×50 ml) and washed with aq. sat. NaCl. The organics were combined, dried over MgSO4 and concentrated to give (Z)-2-{[(6-aminopyridin-2-yl)methoxy]imino}-N′-hydroxy-2-phenylethanimidamide (5 g, 99% yield) as a white solid.

Workup

customthe solvent was evaporated to ¾th
extractionThe residue was extracted with EtOAc (3×50 ml)
washwashed with aq. sat. NaCl
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-87d68c294d4d4b19904178cb80e7d6a2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375010B2

Reaction notes

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