Sodium Acetate → 2-(4-Methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one

HRID 557327

반응식

HRID 557327 반응식
Br[C:2]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:3]=1[C:4]([N:6]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:7][C:8]([CH3:10])=[CH2:9])=[O:5].C(O[Na])=O.CC([O-])=O.[Na+]>CN(C=O)C.[N+](CC)(CC)(CC)CC.[Cl-]>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:6]2[CH2:7][C:8]([CH3:10])([CH3:9])[C:2]3[C:3](=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)[C:4]2=[O:5])=[CH:13][CH:14]=1

참가 물질

6

반응물 3

HCID 517045Sodium AcetateHCID 219593762-Bromo-N-(4-methoxy-benzyl)-N-(2-methyl-allyl)-5-nitro-benzamideHCID 178526064HCID 178526064, 화합물

생성물 1

HCID 219593622-(4-Methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one

시약·촉매·용매 2

HCID 5946Tetraethylammonium Chloride촉매HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

2-Bromo-N-(4-methoxy-benzyl)-N-(2-methyl-allyl)-5-nitro-benzamide (23.4 mmol) was dissolved in DMF (150 ml) and Et4NCl (4.25 g), HCO2Na (1.75 g) and NaOAc (4.99 g) were added. N2 was bubbled through the solution for 10 min, then Pd(OAc)2 (490 mg) was added and the mixture was stirred overnight at 70° C. The mixture was extracted with EtOAc, washed with sat'd NH4Cl, dried over MgSO4, filtered and concentrated until the compound precipitated as a white solid.

후처리

  1. customN2 was bubbled through the solution for 10 min
  2. additionPd(OAc)2 (490 mg) was added
  3. extractionThe mixture was extracted with EtOAc
  4. washwashed with sat'd NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated until the compound
  8. customprecipitated as a white solid

출처 및 근거

ORD 기록
ord-9217d0f748ab45e2a7aafd65ead9adf8
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058445B2

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