Chloride → 4-methyl-2H-isoquinolin-1-one

HRID 2252831

반응식

HRID 2252831 반응식
C(N(CC)CC)C.[Cl-].[CH2:9]([NH:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1I)[CH:10]=[CH2:11]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:11][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:21])[NH:12][CH:9]=1

참가 물질

6

반응물 3

HCID 312ChlorideHCID 8471TriethylamineHCID 2190306N-Allyl-2-iodobenzamide

생성물 1

HCID 126952994-methyl-2H-isoquinolin-1-one

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

Under an N2 atmosphere, 985 ml (7.07 mol) of triethylamine, 892 g (3.21 mol) of tetra-nbutylammonium chloride and 12.77 g (57 mmol) of Pd(OAc)2 are added to 815 g (2.8 mol) of 2-iodo-benzoic acid allylamide in 4.5 l of DMF, and heated to 100° C. After 4 h, cooling is effected to RT, and the mixture is partially concentrated by evaporation on a RE. The residue is partitioned between 5 l of water and 5 l of EtOAc, the water phase is separated and extracted twice with EtOAc. The organic phases are washed with water, 0.1 N HCl, water and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2, EtOAc/toluene 1:1) and crystallisation from toluene yields 4-methyl-2H-isoquinolin-1-one; m.p. 175-176° C.

후처리

  1. temperaturecooling
  2. customis effected to RT
  3. concentrationthe mixture is partially concentrated by evaporation on a RE
  4. customThe residue is partitioned between 5 l of water and 5 l of EtOAc
  5. customthe water phase is separated
  6. extractionextracted twice with EtOAc
  7. washThe organic phases are washed with water, 0.1 N HCl, water and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated by evaporation
  10. customColumn chromatography (SiO2, EtOAc/toluene 1:1) and crystallisation from toluene

출처 및 근거

ORD 기록
ord-ea98753a2da54046847a7daa9bfd0111
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323474B2

연결된 노트

불러오는 중…