Calcium Chloride → 5-Amino-3-chloropyridine-2-carbonitrile

HRID 1441863Notes

Reaction equation

HRID 1441863 reaction equation
[Cl:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[Cl-].[Ca+2].[Cl-]>C(O)C.[Fe]>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([C:11]#[N:12])=[N:4][CH:5]=1

Participants

5

Reactant 2

HCID 5284359Calcium ChlorideHCID 218754953-Chloro-5-nitropicolinonitrile

Product 1

HCID 218750995-Amino-3-chloropyridine-2-carbonitrileYield 48%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

3-Chloro-2-cyano-5-nitropyridine (0.35 g, 1.9 mmol), iron powder (0.56 g, 10 mmol, 325 Mesh) and calcium chloride (0.06 g, 0.55 mmol) were combined in 10 mL of 90% ethanol and as described in example 772B. Purification of the crude product via silica gel chomatography using 10% ether/CH2Cl2 as the eluent gives compound 775D (0.14 g, 43%) as a light brown solid. HPLC: 95.5% at 1.69 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 154.03 [M+H]+.

Workup

  1. customPurification of the crude product via silica gel chomatography

Sources & evidence

ORD record
ord-6ccd59a613034827a00c2c739741d34b
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

Loading…