Ammonium formate → 4-(3-Methoxypyridin-4-yl)-2-(propan-2-yloxy)aniline

HRID 518802Notes

Reaction equation

C([O-])=O.[NH4+].[CH3:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([O:22][CH:23]([CH3:25])[CH3:24])[CH:14]=1>CO.[Pd]>[CH3:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([O:22][CH:23]([CH3:25])[CH3:24])[CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

7.55 g of ammonium formate and 1.5 g of Pd/C (10%) are added to a solution of 5.75 g of 3-methoxy-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridine in 100 ml of methanol. The reaction medium is microwave-heated at 80° C. for 5 minutes. The mixture is filtered on Clarcel, and the Clarcel is rinsed with methanol. The filtrate is concentrated under reduced pressure. The residue is taken up with 60 ml of ethyl acetate and 20 ml of water. The 2 phases are separated, and the aqueous phase is extracted with twice 20 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated, so as to give 5.35 g of 4-(3-methoxypyridin-4-yl)-2-(propan-2-yloxy)aniline in the form of a brown gum.

Workup

filtrationThe mixture is filtered on Clarcel
washthe Clarcel is rinsed with methanol
concentrationThe filtrate is concentrated under reduced pressure
customThe 2 phases are separated
extractionthe aqueous phase is extracted with twice 20 ml of ethyl acetate
dry with materialThe combined organic phases are dried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-cc295b7e7f1049699e53cb41c69d335b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115140B2

Reaction notes

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