Isobutylene → 2-(3-Bromophenyl)-4,4,8-trimethyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile

HRID 1036868

반응식

HRID 1036868 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O.[CH2:20]=[C:21]([CH3:23])[CH3:22].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C.C(OCC)(=O)C>[Br:11][C:12]1[CH:13]=[C:14]([CH:15]2[CH2:20][C:21]([CH3:23])([CH3:22])[C:9]3[C:2](=[C:3]([CH3:10])[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=3)[NH:1]2)[CH:17]=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 8255IsobutyleneHCID 765833-BromobenzaldehydeHCID 2733225Ytterbium triflateHCID 70103164-Amino-3-methylbenzonitrile

생성물 1

HCID 672899872-(3-Bromophenyl)-4,4,8-trimethyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile수율 26.2%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

To a stirred solution of 4-amino-3-methyl-benzonitrile (10.3 g, 78.4 mmol) and 3-bromobenzaldehyde (9.2 mL, 78.4 mmol) in acetonitrile (150 mL) were added isobutene (21.0 mL, 313.5 mmol) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (5.8 g, 9.5 mmol). The resulting mixture was stirred at 85° C. for 18 h in sealed tube. The mixture was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-30% ethyl acetate in petroleum ether) to afford 2-(3-bromo-phenyl)-4,4,8-trimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (7.3 g, 26.1%) as a light yellow oil: LC/MS m/e obsd. (ESI+) [(M+H)+] 355.0 & 357.0.

후처리

  1. washwashed with water (100 mL×2) and brine (100 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 10-30% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-1d2e55a5f4514e8b9eb0a1c1afb69f7f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546427B2

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