Ethyl Acetate → Methyl 2-cyano-6-methylisonicotinate

HRID 2071151

반응식

HRID 2071151 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=O.[CH3:13]COC(C)=O.[NH4+:19].[OH-:20]>CN(C=O)C.[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:20])#[N:19]

참가 물질

7

반응물 3

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 2759833Methyl 2-Chloro-6-methylisonicotinate

생성물 1

HCID 58802283Methyl 2-cyano-6-methylisonicotinate수율 68%

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2.03 g (11 mmol) of methyl 2-chloro-6-methylisonicotinate (Aldrich) in 20 mL of DMF (degassed) was added 1.14 g (9.73 mmol) of Zn(CN)2 and 1.18 g (1.02 mmol) of Pd(PPh3)4. The mixture was stirred at 80° C. for 12.5 h, and EtOAc and 20 mL of 10% NH4OH aqueous solution were added. The organic layer was washed with 20 mL of 10% NH4OH and 20 mL of brine. The combined aqueous layers were reextracted with EtOAc and washed with brine. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 1.3 g of methyl 2-cyano-6-methylisonicotinate in 68% yield.

후처리

  1. washThe organic layer was washed with 20 mL of 10% NH4OH and 20 mL of brine
  2. washwashed with brine
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography (30% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-11532bef617c47be9faf70fd496de537
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

연결된 노트

불러오는 중…