Hydrazine → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid hydrazide

HRID 1516192Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[NH2:25][NH2:26]>C(O)C>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]=1[CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([NH:25][NH2:26])=[O:2])=[CH:5][N:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (1.0 g, 3 mmol), hydrazine (3.09 g, 62 mmol) and ethanol (1 mL) was heated at 90° C. for 5 h. The mixture was cooled and concentrated to give a white residue that was triturated with chloroform and filtered. The filtrate was concentrated to afford the title compound (743 mg, 49%) as a white solid. MS: m/e=325.4 [M+H]+.

Workup

temperatureThe mixture was cooled
concentrationconcentrated
customto give a white residue that
customwas triturated with chloroform
filtrationfiltered
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-7c0ed4e1cb6742289f5fe5ef115d9b1e
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227461B2

Reaction notes

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