Stannous Chloride → 4-Chloro-3-(pyrid-3-yl)aniline

Reaction equation

[Sn](Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1>>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

Reactant 2

HCID 24479Stannous Chloride

HCID 223295393-(2-Chloro-5-nitrophenyl)pyridine

Product 1

HCID 121019664-Chloro-3-(pyrid-3-yl)anilineYield 87%

Procedure

Tin(II) chloride (11.87 g, 62.6 mmol) and 3-(2-chloro-5-nitrophenyl)pyridine (3.53 g, 15.1 mmol) were reacted as described in Example 62 to give 4-chloro-3-(pyridin-3-yl)phenylamine (2.69 g, 87%) which was used without purification on silica: δH (360 MHz, CDCl3) 6.65-6.70 (2H, m), 7.26 (1H, dt, J 8.5 and 1.1), 7.33 (1H, dd, J 7.8 and 4.8), 7.77 (1H, dt, J 7.8 and 1.9), 8.59 (1H, dd, J 4.8 and 1.6), 8.66 (1H, d, J 1.8); m/z (ES+) 205, 207 (3:1) (M++H).

Sources & evidence

ORD record: ord-d79a0cc0c0ef4926bf45fb1657d532d5
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900215B2

Reaction notes

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