(R)-3-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine → (R)-3-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

HRID 2266657Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

Iron (365 mg) was added to a stirred solution of 3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-2-nitropyridine (321 mg, 0.97 mmol) in a mixture of EtOH (2 mL) and 2M HCl (0.2 mL) at 0° C. The resulting solution was heated to 85° C. for 2 h. Celite (0.5 g) was added to the cooled reaction mixture. This mixture was filtered over a bed of celite and evaporated to give the title compound as a dark oil. MS (APCI) (M+H)+ 301.

Workup

additionCelite (0.5 g) was added to the cooled reaction mixture
filtrationThis mixture was filtered over a bed of celite
customevaporated

Sources & evidence

ORD record: ord-f3d6a0a5af744532bec6788bb24eac96
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858643B2

Reaction notes

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