O-Methylhydroxylamine → furo[2,3-c]pyridazin-5(6H)-one O-methyl oxime

HRID 1508194Notes

Reaction equation

[N:1]1[C:6]2[O:7][CH2:8][C:9](=O)[C:5]=2[CH:4]=[CH:3][N:2]=1.[CH3:11][O:12][NH2:13].CC([O-])=O.[Na+]>CCO>[CH3:11][O:12][N:13]=[C:9]1[C:5]2[CH:4]=[CH:3][N:2]=[N:1][C:6]=2[O:7][CH2:8]1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of furo[2,3-c]pyridazin-5(6H)-one (4.81 mmol) in 30 mL EtOH were added O-methyl-hydroxylamine (9.62 mmol) and NaOAc (9.62 mmol). After heating to 30° C. for 4.5 h the reaction mixture was concentrated in vacuo to half of its volume. Water and DCM were added and the aqueous phase was extracted with DCM (3×). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (1/1) gives the desired product as beige solid;

Workup

concentrationwas concentrated in vacuo to half of its volume
additionWater and DCM were added
extractionthe aqueous phase was extracted with DCM (3×)
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo
customPurification by CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record: ord-851114f8ad8b4b6d851cb0ff957e60ef
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221832B2

Reaction notes

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