Ethanol → 4-[5-(Diethoxymethyl)-1-methyl-1H-pyrazol-3-yl]aniline

HRID 456792Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[C:5]#[C:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)=O)[CH3:2].[CH3:21][NH:22][NH2:23].C(O)C.[H][H]>[Pd].C1COCC1>[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[C:5]1[N:22]([CH3:21])[N:23]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

4,4-Diethoxy-1-(4-nitrophenyl)but-2-yn-1-one (Intermediate 9, 5.77 g, 22.4 mmol), methylhydrazine (1.2 ml, 22.4 mmol), and ethanol (100 ml) were combined and warmed at 70° C. for 45 min. THF (50 ml) and palladium on carbon (10%, 100 mg) were added. The suspension was stirred under 1 atmosphere of hydrogen gas for 16 hrs. The mixture was filtered and evaporated to give the title compound as a light yellow solid (5.54 g).

Workup

filtrationThe mixture was filtered
customevaporated

Sources & evidence

ORD record: ord-b50907e3867244308c50ddc9a92266a3
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186738B2

Reaction notes

Loading…