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Triphenylphosphine → 1-Aminoisoquinoline-7-carbonitrile

HRID 1008550
ノート
印刷プレビュー

反応式

HRID 1008550 の反応式
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OS(C(F)(F)F)(=O)=O)[CH:10]=2)[CH:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:39][N:40]1CCCC1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[C-]#N.[Zn+2].[C-]#N>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:39]#[N:40])[CH:10]=2)[CH:5]=[CH:4][N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 13387N-methyl-2-pyrrolidoneHCID 54109345Trifluoromethanesulfonic acid 1-amino-isoquinolin-7-yl ester

生成物 1

HCID 226658481-Aminoisoquinoline-7-carbonitrile収率 94%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 167845
palladium(II) acetate
触媒

実験手順

Palladium acetate (0.9 g) was added to a heated mixture of trifluoromethanesulfonic acid 1-amino-isoquinolin-7-yl ester (5.8 g), zinc cyanide (2.3 g) and triphenylphosphine (1.0 g) in 75 mL of N-methyl-pyrrolidone at 190° C. (exothermic!). Stirring was continued at 190° C. for 2 h. Precipitated material was removed by filtration and discarded. Ethyl acetate was added and the organic mixture washed with 2N aqueous ammonia, water and brine and dried (Na2SO4). Filtration and concentration afforded a brownish oil, which was purified by silica chromatography (ethyl acetate/isohexane=3/7, 4/6, 5/5, 6/4, 7/3, 8/2) to give 3.2 g (94%) of the title compound as yellow crystals. M.p. 183-186° C.

後処理

  1. customPrecipitated material was removed by filtration
  2. additionEthyl acetate was added
  3. washthe organic mixture washed with 2N aqueous ammonia, water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration and concentration
  6. customafforded a brownish oil, which
  7. customwas purified by silica chromatography (ethyl acetate/isohexane=3/7, 4/6, 5/5, 6/4, 7/3, 8/2)

出典と根拠

ORDレコード
ord-5cb46dbe83bc49f9a5aa664769aac54e
出典データセット
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06797710B2

反応ノート

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