Hydroxyamine hydrochloride → 3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehyde oxime

HRID 985517Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]=O)=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:2]=1.Cl.[NH2:25][OH:26]>C(O)C.CO.ClCCl>[NH3:1].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]=[N:25][OH:26])=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxaldehyde (0.30 g, 1.0 mmol) and hydroxylamine hydrochloride (0.208 g, 3.0 mmol) were suspended in ethanol (15 ml) then heated at 60° C. for 45 min. The mixture was diluted with 50% methanol in dichloromethane (200 ml) and pre-adsorbed onto silica. Purification by flash column chromatography on silica gel eluting with dichloromethane/methanol/conc. ammonia (95:5:0.5) gave the title compound (297 mg, 94%) as a white foam. Further purification of this material by preparative thin-layer chromatography eluting with dichloromethane/methanol/conc. ammonia (95:5:0.5) gave (E)-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxaldehyde oxime as a white solid followed by (Z)-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxaldehyde oxime also as a white solid.

Workup

customPurification by flash column chromatography on silica gel eluting with dichloromethane/methanol/conc

Sources & evidence

ORD record: ord-419302785f934b5883afbb2c4b92614e
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872731B2

Reaction notes

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