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

HRID 238708Notes

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 7b (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 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 7c (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-fe66a76792334702bdff2a08fbf29211
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642637B2

Reaction notes

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