Methylamine → 6-Chloro-2-(methylamino)-3-nitrobenzonitrile

HRID 562420ノート

反応式

HRID 562420 の反応式
Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[C:3]=1[C:4]#[N:5].[CH3:14][NH2:15]>C(OCC)(=O)C>[Cl:13][C:6]1[C:3]([C:4]#[N:5])=[C:2]([NH:15][CH3:14])[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=1

参加物

4

反応物 2

HCID 6329Methylamine2 回HCID 44619322,6-Dichloro-3-nitrobenzonitrile

生成物 1

HCID 112180896-Chloro-2-(methylamino)-3-nitrobenzonitrile収率 96%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

To a 1 L two-neck round bottom flask was added 2,6-dichloro-3-nitrobenzonitrile (11.1 g, 51.1 mmol) followed by ethyl acetate (102 mL). The flask was equipped with an internal thermometer and magnetic stir bar and cooled to 5° C. by immersion into an ice bath. Methylamine was added dropwise to the cooled reaction mixture as a 40% aqueous solution (8.9 mL, 115 mmol) with vigorous stirring. The reaction mixture was stirred for an additional 3 hours with cooling, after which more methylamine (1.8 mL, 23 mmol) was added. The reaction vessel was removed from the ice bath and stirred for an additional 1.5 hours. To the reaction mixture was added water (30 mL) followed immediately by hexane (45 mL) and the resulting slurry was stirred for 15 minutes. The solid was recovered by filtration and washed with water followed by methanol to provide 6-chloro-2-methylamino-3-nitro-benzonitrile (10.49 g, 96%) as a bright yellow solid, which was used directly without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.55-8.53 (m, 1H), 8.28 (d, 1H, J=9.0 Hz), 6.95 (d, 1H), J=9.0 Hz), 3.30 (d, 1H, J=5.5 Hz).

後処理

  1. customThe flask was equipped with an internal thermometer and magnetic stir bar
  2. temperaturewith cooling
  3. customThe reaction vessel was removed from the ice bath
  4. stirringstirred for an additional 1.5 hours
  5. additionTo the reaction mixture was added water (30 mL)
  6. stirringthe resulting slurry was stirred for 15 minutes
  7. filtrationThe solid was recovered by filtration
  8. washwashed with water

出典と根拠

ORDレコード
ord-ef2a857b0c26436187b6fbf2395420f0
出典データセット
uspto-grants-2011_11
特許番号
US08067395B2

反応ノート

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