3-Cyano-2,6-dichloro-4-methylpyridine → (E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile

HRID 1034943

反応式

HRID 1034943 の反応式
[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>C(O)(C)C>[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6](/[CH:11]=[CH:14]/[N:15]([CH3:17])[CH3:16])[C:3]=1[C:4]#[N:5]

参加物

4

反応物 2

HCID 701313-Cyano-2,6-dichloro-4-methylpyridineHCID 78373Dimethylformamide dimethyl acetal

生成物 1

HCID 58093913(E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
65 °C

実験手順

To 2,6-dichloro-4-methylnicotinonitrile (20.3 g, 0.108 mol) in 200 mL of isopropyl alcohol is added N,N-dimethylformamide dimethylacetal (14.4 mL, 0.108 mol) and the reaction is stirred at 65° C. for 18 hrs. After the reaction is cooled to ambient temperature, the precipitate is collected by filtration, washed with 50 mL of isopropyl alcohol, and air dried giving (E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile as a yellow solid. MS (ES+) calcd. 242.02. found 242.10 (MH+). H-NMR (600 MHz, DMSO-d6) 2.90 (br.s, 3H), 3.17 (br.s, 3H), 5.05 (d, J=12.6 Hz, 1H), 7.61 (s, 1H), 8.09 (d, J=12.6 Hz, 1H).

後処理

  1. temperatureAfter the reaction is cooled to ambient temperature
  2. filtrationthe precipitate is collected by filtration
  3. washwashed with 50 mL of isopropyl alcohol, and air
  4. customdried

出典と根拠

ORDレコード
ord-6a049bcd94eb4f10a1237941cfb83371
出典データセット
uspto-grants-2013_10
特許番号
US08546370B2

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