Hydrazine → HCID 66615831, compound

HRID 76072Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2].O.[C:23]([OH:27])(=O)[CH:24]=O.[OH-].[NH4+:29].[NH2:30]N>O.C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:24][C:23](=[O:27])[NH:30][N:29]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of [4-(4-acetyl-phenyl)-cyclohexyl]-acetic acid ethyl ester (17 g, 59 mmol, 1.0 equiv) in 100 Ml glacial acetic acid was added glyoxylic acid monohydrate (5.4 g, 59 mmol, 1.0 equiv) as a solid. The solution was heated to 100° C. for 2 h. The mixture was then cooled to 40° C., then 75 Ml water was added followed by 120 Ml of a 28% ammonium hydroxide solution until the Ph was measured to be 8. Hydrazine (2.0 Ml, 65 mmol, 1.1 equiv) was then added via syringe, and the reaction was then heated to 95° C. for 2 hr. Upon cooling to room temperature, a solid precipitate was filtered off to afford the title compound in addition to the uneliminated product {4-[4-(5-hydroxy-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-cyclohexyl}-acetic acid ethyl ester. This mixture was taken into the next step without further purification. (M+H)+341.2.

Workup

temperatureThe mixture was then cooled to 40° C.
temperaturethe reaction was then heated to 95° C. for 2 hr
temperatureUpon cooling to room temperature
filtrationa solid precipitate was filtered off

Sources & evidence

ORD record: ord-adf7c16b46704be0b95324c838934bb7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835451B2

Reaction notes

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