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

HRID 2377051ノート

反応式

HRID 2377051 の反応式
[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

参加物

5

反応物 2

HCID 78373Dimethylformamide dimethyl acetal2 回HCID 20717632Methyl 4-methyl-5-nitropyridine-2-carboxylate2 回

生成物 1

HCID 86602115Methyl 4-[(E)-2-(dimethylamino)vinyl]-5-nitropyridine-2-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-55ff803c745e41c0bfa4cf019e266ff6
出典データセット
uspto-grants-2008_12
特許番号
US07468375B2

反応ノート

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