Tert-butyl (2,6-dichloro-3-nitropyridin-4-yl)carbamate → Tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate

HRID 1852811Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl (2,6-dichloro-3-nitropyridin-4-yl)carbamate (65 g, 0.212 mol) was added to a mixture of Raney-Ni (12.5 g) in ethanol (1.5 L) under H2. The mixture was stirred at 50° C. for 3 h. TLC (petroleum/ethyl acetate=5:1) showed that most of the tert-butyl (2,6-dichloro-3-nitropyridin-4-yl)carbamate was consumed. The mixture was filtered, and the filtrate was concentrated to give crude tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate, which was used for the next step without further purification. 1H NMR (400 MHz, CDCl3) δ: 7.84 (s, 1H), 6.85 (s, 1H), 1.54 (s, 9H).

Workup

customwas consumed
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-b26154ee228b43d5a1aa5cad0cbdb0a4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962611B2

Reaction notes

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