2-Chloro-5-nitro-3-(trifluoromethyl)pyridine → 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

HRID 1441855Notes

Reaction equation

HRID 1441855 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:12]([O-])=O)=[CH:4][N:3]=1>[Fe]>[NH2:12][C:5]1[CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

3

Reactant 1

HCID 38491402-Chloro-5-nitro-3-(trifluoromethyl)pyridine

Product 1

HCID 135322446-Chloro-5-(trifluoromethyl)pyridin-3-amineYield 73.3%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

2-Chloro-5-nitro-3-trifluoromethylpyridine (0.16 g, 0.68 mmol) and iron powder (0.2 g, 3.42 mmol, 325 Mesh) were reacted as described in example 762D. Purification of the crude product by Prep-TLC using 10% ether/CH2Cl2 as eluent gave compound 766B (0.098 g, 73%) as a yellow solid. HPLC: 89% at 2.52 min(YMC S5 ODS column) eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm. MS (ES): m/z 197.01 [M+H]+.

Workup

  1. customPurification of the crude product by Prep-TLC

Sources & evidence

ORD record
ord-5039b8b8024d4bb1bcaf41d7013eaa6f
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

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