N,N-二甲基甲酰胺 → 异喹啉-5-甲醛

HRID 479469

反应方程式

HRID 479469 反应方程式
C([Li])CCC.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][N:8]=1.CN([CH:20]=[O:21])C.C1([Li])C2C(=CC=CC=2)C=CN=1.[NH4+].[Cl-]>CCOCC.C1COCC1.C(O)C.CCOC(C)=O>[CH:7]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:20]=[O:21])[C:11]=2[CH:10]=[CH:9][N:8]=1

参与物

10

反应物 5

HCID 6228N,N-二甲基甲酰胺HCID 25517氯化铵HCID 6409631-溴异喹啉HCID 178418339正丁基锂HCID 178506776HCID 178506776，化合物

产物 1

HCID 7016853异喹啉-5-甲醛收率 64%

试剂、催化剂与溶剂 4

HCID 702乙醇溶剂2 次HCID 3283乙醚溶剂HCID 8028四氢呋喃溶剂3 次HCID 8857乙酸乙酯溶剂

反应条件

温度
-78 °C

实验过程

To a solution of n-butyllithium (19.3 mL of 2.5M in hexanes, 48 mmol) in a mixture of ether (80 mL) and THF (80 mL) at −78° C. was added dropwise a solution of bromoisoquinoline (5.0 g, 24 mmol) in THF (10 mL). The reaction mixture was stirred at −78° C. under argon for 30 minutes. Following the general procedures described by Pearson, et al., in J. Heterocycl. Chem., Vol. 6 (2), pp. 243-245 (199), a solution of DMF (3.30 g, 45 mmol) in THF (10 mL) was cooled to −78° C. and quickly added to the isoquinolyllithium solution. The mixture was stirred at −78° C. for 15 minute. Ethanol (20 mL) was added followed by saturated NH4Cl solution. The resulting suspension was warmed to room temperature. The organic layer, combined with the ether extraction layer, was dried over Na2SO4. A pale yellow solid (2.4 g, 15 mmol, 64% yield) was obtained from chromatography (SiO2 Type-H, 50% EtOAc in hexanes) and recrystallization (ethanol): mp 114-116° C.;

后处理

  1. stirringThe mixture was stirred at −78° C. for 15 minute
  2. temperatureThe resulting suspension was warmed to room temperature
  3. extractionThe organic layer, combined with the ether extraction layer
  4. dry with materialwas dried over Na2SO4

来源与证据

ORD记录
ord-3e5d05227a1448bb9b18bac65890476a
来源数据集
uspto-grants-2003_11
专利号
US06645975B1

关联笔记

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