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

HRID 1833257ノート

反応式

HRID 1833257 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 220483501-Bromo-6,7-dimethoxyisoquinoline-4-carbonitrile収率 75%

試薬・触媒・溶媒 1

HCID 7519Anisole溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-db4c3ac554c84a4f9261da8d34d56b0b
出典データセット
uspto-grants-2006_06
特許番号
US07067529B2

反応ノート

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