Acetylacetone → HCID 178468308, compound

HRID 1407083Notes

Reaction equation

[CH:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:14]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[C:23]([CH2:26][C:27](=[O:29])[CH3:28])(=[O:25])[CH3:24]>C(O)(=O)C.Cl.O.C(O)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH:11][N:14]=[C:26]([C:27](=[O:29])[CH3:28])[C:23](=[O:25])[CH3:24])=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-cyclohexylaniline (500 mg, 2.86 mmol) in 10 mL of acetic acid and 2 mL of concentrated hydrochloride solution, sodium nitrite (237 mg, 3.43 mmol) in 4 mL of water was added dropwise at 0° C., and the mixture was stirred at 0° C. for 1 h. Then to the reaction mixture was added dropwise a solution of sodium acetate (703 mg, 8.58 mmol) and acetylacetone (372 mg, 3.72 mmol) in 10 mL of ethanol and 6 mL of water. The mixture was stirred at room temperature overnight, filtered, washed with water, EtOH/H2O (1:1) and hexane, and dried to give 3-[(4-cyclohexylphenyl)hydrazono]pentane-2,4-dione (420 mg, 51%).

Workup

stirringThe mixture was stirred at room temperature overnight
filtrationfiltered
washwashed with water, EtOH/H2O (1:1) and hexane
customdried

Sources & evidence

ORD record: ord-d53b1a978225409db368965a9e1e644a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916566B2

Reaction notes

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