Pyridine → HCID 70088544, compound

HRID 2216744Notes

Reaction equation

HRID 2216744 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([NH2:11])=O)[N:6]=[C:5]([C:12]([NH2:14])=O)[CH:4]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C=CC=CC=1>ClCCl>[C:9]([C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([C:12]#[N:14])[N:6]=1)#[N:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 4309684HCID 4309684, compound

Product 1

HCID 70088544HCID 70088544, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-methoxypyridine-2,6-dicarboxamide (900 mg, 4.6 mmol) was mixed with trifluoroacetic anhydride (2.32 g, 11.1 mmol) and pyridine (1.6 g, 20.2 mmol) in dichloromethane (20 mL) and stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane and washed with water. Standard work up, afforded 461 mg of 2,6-dicyano-4-methoxypyridine.2,6-Dicyano-4-methoxypyridine (460 mg, 2.89 mmol) and 5M hydroxylamine hydrochloride (0.578 mL, 2.89 mmol) in ethanol (3 mL) and 1 N sodium hydroxide (2.89 mL, 2.89 mmol), were stirred at room temperature overnight. Standard work up afforded 180 mg (32.4%) of 6-cyano-4-methoxypyrid-2-yl-amidoxime.

Workup

  1. washwashed with water

Sources & evidence

ORD record
ord-cf93df7155d34f63b1cbc52516d4fa00
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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