Hydrazine hydrate (1:1) → 5-(4-benzyloxy-phenyl)-6-butyl-2H-pyridazin-3-one

HRID 2168590Notes

Reaction equation

C([O:3][C:4](=O)[CH:5](O)[CH:6]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[C:7](=O)[CH2:8][CH2:9][CH2:10][CH3:11])C.O.[NH2:30][NH2:31]>C(O)(=O)C>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:6]2[C:7]([CH2:8][CH2:9][CH2:10][CH3:11])=[N:31][NH:30][C:4](=[O:3])[CH:5]=2)=[CH:14][CH:15]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3-(4-benzyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester (28.08 mmol, 10.8 g) and hydrazine hydrate (15 mL) in acetic acid (45 mL) was stirred at 120° C. for 4 h. The reaction mixture was concentrated under reduced pressure and to the residue was added water (200 mL). This was extracted with DCM (3×200 mL), and the combined organic layer was dried and concentrated under reduced pressure. The resultant residue was purified by flash silica gel column chromatography eluting with 50% ethyl acetate in hexanes to afford 5-(4-benzyloxy-phenyl)-6-butyl-2H-pyridazin-3-one.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure and to the residue
additionwas added water (200 mL)
extractionThis was extracted with DCM (3×200 mL)
customthe combined organic layer was dried
concentrationconcentrated under reduced pressure
customThe resultant residue was purified by flash silica gel column chromatography
washeluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-c7dc70fb87de466494bc9e356b562a5b
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045461B2

Reaction notes

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