Pyridine → HCID 70088544, compound

HRID 431849Notes

Reaction equation

HRID 431849 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 1N 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-3801f31cf37c42aaa0bd517ddd75f46a
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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