Ethanol → 4-(4-Aminophenoxy)-2-butyrylaminopyridine

HRID 387931Notes

Reaction equation

[C:1]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH:10]=[CH:9][N:8]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[Cl-].[NH4+].C(O)C.CN(C)C=O>[Fe].O>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH:12]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 0.6 g of 2-butyrylamino-4-(4-nitrophenoxy)pyridine, 1.2 g of iron powder, 2.8 g of ammonium chloride, 10 ml of ethanol, 10 ml of dimethylformamide and 5 ml of water was vigorously stirred at 100° C. for 10 minutes. The reaction was filtered with celite, the solvent was distilled off under reduced pressure, and then water was added to the filtrate and extraction was performed with ethyl acetate. The extract was dried over magnesium sulfate and the solvent distilled off under reduced pressure to obtain 0.6 g of the target substance as a light yellow solid.

Workup

filtrationThe reaction was filtered with celite
distillationthe solvent was distilled off under reduced pressure
additionwater was added to the filtrate and extraction
dry with materialThe extract was dried over magnesium sulfate
distillationthe solvent distilled off under reduced pressure
customto obtain 0.6 g of the target substance as a light yellow solid

Sources & evidence

ORD record: ord-fbf189f6177642c09de1423dc7d6e9e0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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