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

HRID 562420노트

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HRID 562420 반응식
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

참가 물질

4

반응물 2

HCID 6329Methylamine2회HCID 44619322,6-Dichloro-3-nitrobenzonitrile

생성물 1

HCID 112180896-Chloro-2-(methylamino)-3-nitrobenzonitrile수율 96%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ef2a857b0c26436187b6fbf2395420f0
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067395B2

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