Ammonium formate → HCID 86698038, compound

HRID 518888Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([O:16][CH:17]([CH3:19])[CH3:18])[CH:8]=2)=[N:3]1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([O:16][CH:17]([CH3:19])[CH3:18])[CH:8]=2)=[N:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

In a microwave tube, 860 mg of 1-methyl-3-[4-nitro-3-(propan-2-yloxy)phenyl]-1H-pyrazole are introduced into 30 ml of methanol. 1.25 g of ammonium formate and 1.05 g of Pd/C (10%) are added. The reaction medium is microwave-heated at 80° C. for 3 times 7 minutes. The mixture is filtered on Clarcel and the Clarcel is rinsed with methanol. The filtrate is concentrated under reduced pressure and the residue is taken up with 30 ml of ethyl acetate and 3 ml of water. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel, elution being carried out with a dichloromethane/methanol (95/5) mixture, so as to obtain 110 mg of 4-(1-methyl-1H-pyrazol-3-yl)-2-(propan-2-yloxy)aniline in the form of a purple oil.

Workup

filtrationThe mixture is filtered on Clarcel
washthe Clarcel is rinsed with methanol
concentrationThe filtrate is concentrated under reduced pressure
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue is purified by flash chromatography on silica gel, elution

Sources & evidence

ORD record: ord-95f386dddc104f34b8a9bd6774e91cdc
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115140B2

Reaction notes

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