Dichloromethane → 1-Bromo-6,7-dimethoxyisoquinoline-4-carbonitrile

HRID 1833257노트

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HRID 1833257 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=O)[NH:8][CH:7]=[C:6]2[C:16]#[N:17].P(Br)(Br)([Br:20])=O.C(Cl)Cl>C1(OC)C=CC=CC=1>[Br:20][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=2)[C:6]([C:16]#[N:17])=[CH:7][N:8]=1

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 24613Phosphorus oxybromideHCID 220483556,7-Dimethoxy-1-oxo-1,2-dihydroisoquinoline-4-carbonitrile

생성물 1

HCID 220483501-Bromo-6,7-dimethoxyisoquinoline-4-carbonitrile수율 75%

시약·촉매·용매 1

HCID 7519Anisole용매

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온도
80 °C

실험 절차

The mixture of 6,7-Dimethoxy-1-oxo-1,2-dihydro-isoquinoline-4-carbonitrile (8 g, 35 mmol) and phosphorus oxybromide (70 g, 244 mmol) in anisole (30 mL) was heated to 80° C. for 12 h. The solvent and excess POBr3 were removed by rotary evaporator. The resulting solid was washed with hexane and dried. The solid was slowly added to ice and the product was extracted with chloroform. The organic layer was washed with saturated aqueous sodium carbonate solution, saturated aqueous sodium chloride solution (20 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford a brown solid. Flash chromatography (Merck Silica gel 60, 70–230 mesh, methylenechloride) afforded 1-Bromo-6,7-dimethoxy-isoquinoline-4-carbonitrile (7.5 g, 75%) as a brown solid. LC-MS m/e calcd for C12H9BrN2O2 (MH+) 293, found 293.

후처리

  1. customThe solvent and excess POBr3 were removed by rotary evaporator
  2. washThe resulting solid was washed with hexane
  3. customdried
  4. additionThe solid was slowly added to ice
  5. extractionthe product was extracted with chloroform
  6. washThe organic layer was washed with saturated aqueous sodium carbonate solution, saturated aqueous sodium chloride solution (20 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto afford a brown solid

출처 및 근거

ORD 기록
ord-db4c3ac554c84a4f9261da8d34d56b0b
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067529B2

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