Acrylonitrile → HCID 69070739, 화합물

HRID 347431노트

반응식

HRID 347431 반응식
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17](I)=[C:16]3[O:21][CH2:22][O:23][C:15]=13)=[CH:10][C:9]([O:24][CH3:25])=[C:8]([O:26][CH3:27])[CH:7]=2)#[N:2].[C:28](#[N:31])[CH:29]=[CH2:30].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH:30]=[CH:29][C:28]#[N:31])=[C:16]3[O:21][CH2:22][O:23][C:15]=13)=[CH:10][C:9]([O:24][CH3:25])=[C:8]([O:26][CH3:27])[CH:7]=2)#[N:2]

참가 물질

6

반응물 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 10310906HCID 10310906, 화합물

생성물 1

HCID 69070739HCID 69070739, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
115 °C

실험 절차

A mixture of 3-cyano-4-(4-iodo-2,3-methylenedioxyanilino)-6,7-dimethoxyquinoline (0.2 g), acrylonitrile (0.2 ml), triethylamine (0.2 ml), palladium(II) acetate (0.01 g) and DMF (2 ml) was stirred and heated to 115° C. for 3 hours. The reaction mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of hexane and ethyl acetate as eluent. The material so obtained was triturated under diethyl ether. There was thus obtained the title compound, in the form of a 4:1 mixture of trans and cis isomers and as a yellow solid (0.095 g); NMR Spectrum: (DMSOd6, data relating to the major trans isomer) 3.91 (s, 3H), 3.93 (s, 3H), 6.12 (s, 2H), 6.26 (d, 1H), 6.88 (d, 1H), 7.14 (d, 1H), 7.35 (s, 1H), 7.56 (d, 1H), 7.7 (s, 1H), 8.51 (s, 1H), 9.7 (s, 1H); Mass Spectrum: M+H+ 401.

후처리

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. temperatureincreasingly polar mixtures of hexane and ethyl acetate as eluent
  4. customThe material so obtained
  5. customwas triturated under diethyl ether

출처 및 근거

ORD 기록
ord-7f765a5edde44d1fa4bfeeba15e4e69c
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173135B2

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