Ethyl Acetoacetate → 3-Methyl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-1H-pyrazol-5(4H)-one

HRID 384297Notes

Reaction equation

[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[NH:11][NH2:12].[C:13](OCC)(=[O:18])[CH2:14][C:15]([CH3:17])=O>C(O)(=O)C>[CH3:17][C:15]1[CH2:14][C:13](=[O:18])[N:11]([C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=3[CH:1]=2)[N:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(5,6,7,8-Tetrahydro-naphthalen-2-yl)-hydrazine 3h (2.0 g, 12.3 mmol) was dissolved in 50 mL of acetic acid followed by addition of ethyl acetoacetate (1.57 mL, 12.3 mmol). The reaction mixture was heated to 100° C. overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound 5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 3i (1.58 g, yield 56.2%) as a colourless oil.

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-8e62fd574c6d43858faeecea0d18407f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367710B2

Reaction notes

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