Dimethylformamide dimethyl acetal → Methyl 4-[(E)-2-(dimethylamino)vinyl]-5-nitropyridine-2-carboxylate

HRID 2377051Notes

Reaction equation

[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>C(#N)C.CN(C=O)C>[CH3:17][N:18]([CH3:20])/[CH:19]=[CH:1]/[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Method 1. A mixture of methyl 4-methyl-5-nitropyridine-2-carboxylate (3.5 g, 17.8 mmol), dimethylformamide dimethylacetal (DMF-DMA) (3.6 ml, 1.5 eq) in acetonitrile (35 mL) was heated in a microwave at 140° C. for 20 min. The solvent was removed. The residue (5.1 g) was carried onto the next step without further purification. Method 2. A mixture of methyl 4-methyl-5-nitropyridine-2-carboxylate (39.5 g, 0.19 mol) and DMF-DMA (30.6 g, 0.26 mol, 1.35 eq) in DMF (470 mL) was heated to 90° C. for 30 min. The solvent was removed in vacuo. The residue (78 g) was used without further purification in the next step.

Workup

customThe solvent was removed
customThe residue (5.1 g) was carried onto the next step without further purification
temperaturewas heated to 90° C. for 30 min
customThe solvent was removed in vacuo
customThe residue (78 g) was used without further purification in the next step

Sources & evidence

ORD record: ord-55ff803c745e41c0bfa4cf019e266ff6
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468375B2

Reaction notes

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