Ethanol → 4-(4-Aminophenoxy)-N-(cyclopropylmethyl)picolinamide

HRID 387928

Reaction equation

[CH:1]1([CH2:4][NH:5][C:6]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[O:7])[CH2:3][CH2:2]1.[Cl-].[NH4+].C(O)C.CN(C)C=O>[Fe].O>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([C:6]([NH:5][CH2:4][CH:1]3[CH2:3][CH2:2]3)=[O:7])[CH:13]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

After adding 0.35 g of 2-[(cyclopropylmethyl)aminocarbonyl]-4-(4-nitrophenoxy)pyridine to a mixture of 0.7 g of iron powder, 1.4 g of ammonium chloride, 10 ml of ethanol, 10 ml of dimethylformamide and 5 ml of water, the mixture was vigorously stirred at 100° C. for 20 minutes. The reaction solution was filtered with celite and the solvent was distilled off under reduced pressure to obtain 0.37 g of the target substance as a light brown oil.

Workup

filtrationThe reaction solution was filtered with celite
distillationthe solvent was distilled off under reduced pressure
customto obtain 0.37 g of the target substance as a light brown oil

Sources & evidence

ORD record: ord-446d7461e1b447af9ccf115e83b334c2
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Linked notes

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