Sodium hydride → HCID 24999503, compound

HRID 1807473Notes

Reaction equation

HRID 1807473 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[H-].[Na+].[C:14](Cl)(=[O:23])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.CCOC(C)=O>[CH:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:14](=[O:23])[CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 64801Benzenepropanoyl chlorideHCID 5889916-Aminoisoquinoline

Product 1

HCID 24999503HCID 24999503, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 6-aminoisoquinoline in DMF cooled to 0° C. was added NaH and the solution was stirred for 30 minutes at 0° C. Then hydrocinnamoyl chloride was added and the mixture was stirred for 4 hours at room temperature. The mixture was diluted with EtOAc, extracted with NaHCO3(sat), dried (Na2SO4), filtered and evaporated. Column chromatography (SiO2, 10% hexanes/EtOAc) gave N-(isoquilin-6-yl)-3-phenylpropanamide (E2).

Workup

  1. stirringthe mixture was stirred for 4 hours at room temperature
  2. extractionextracted with NaHCO3(sat)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-49205f05e4944bf9adebde00d6ed31e3
Source dataset
uspto-grants-2013_01
Patent number
US08357699B2

Reaction notes

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