2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Cyano-3,4-dimethyl-5-nitropyridine

HRID 1441860노트

반응식

HRID 1441860 반응식
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([N+:10]([O-:12])=[O:11])=[CH:5][N:4]=1)#[N:2].[CH3:13][Mg]Br.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1COCC1>[C:1]([C:3]1[C:8]([CH3:9])=[C:7]([CH3:13])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][N:4]=1)#[N:2]

참가 물질

5

반응물 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 124040403-Methyl-5-nitropicolinonitrileHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 218752092-Cyano-3,4-dimethyl-5-nitropyridine수율 42.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

2-Cyano-3-methyl-5-nitropyridine (0.33 g, 2 mmol) was dissolved in 10 mL of THF and cooled in a dry ice/acetone bath under nitrogen. Methylmagnesium bromide (1.33 mL, 4 mmol) was added via syringe over five mins. The reaction was stirred for 2 h at −70° C. DDQ (0.068 g, 3 mmol) in 7 mL of THF was added and the mixture warmed to 25° C. The solvent was removed in vacuo and the residue was purified by silica gel chomatography using CH2Cl2 as the eluent to give compound 773A (0.15 g, 42%) as a red oil.

후처리

  1. temperaturecooled in a dry ice/acetone bath under nitrogen
  2. temperaturethe mixture warmed to 25° C
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica gel chomatography

출처 및 근거

ORD 기록
ord-b70fdb78a55b4395a1bda1edeb19fda0
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655689B2

반응 노트

불러오는 중…