Acetylacetone → 4-(3,5-dimethyl-1H-pyrazol-1-yl)-3-hydroxyphenyl acetate

HRID 337360

Reaction equation

C[C:2]1[CH:7]=[CH:6]C(S(O)(=O)=O)=[CH:4][CH:3]=1.[C:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][NH2:23])=[C:18]([OH:24])[CH:17]=1)(=[O:14])[CH3:13].C(OC1C=CC(N)=C(O)C=1)(=O)C.C(CC(=O)C)(=O)C>>[C:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:7]([CH3:6])=[CH:2][C:3]([CH3:4])=[N:23]2)=[C:18]([OH:24])[CH:17]=1)(=[O:14])[CH3:13]

Participants

Reactant 3

HCID 31261Acetylacetone

HCID 197705154-Amino-3-hydroxyphenyl acetate

HCID 867032644-Hydrazinyl-3-hydroxyphenyl acetate 4-methylbenzenesulfonate

Product 1

HCID 867032634-(3,5-dimethyl-1H-pyrazol-1-yl)-3-hydroxyphenyl acetateYield 52.8%

Procedure

330 mg of the title compound was prepared in a manner similar to Example 54b) by using 4-hydrazinyl-3-hydroxyphenyl acetate 4-methylbenzenesulfonate (0.9 g), which was prepared from 4-amino-3-hydroxyphenyl acetate (1.0 g) in a manner similar to Example 54a), and acetylacetone (0.9 g).

Sources & evidence

ORD record: ord-2c512ac043bc473fbfb08611a07be3b5
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889727B2

Linked notes

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