1,2-Dichloroethane → HCID 59205709, compound

HRID 1663348Notes

Reaction equation

HRID 1663348 reaction equation
[Cl:1][CH2:2][C:3]([OH:5])=O.C(Cl)CCl.[Cl:10][C:11]1[C:20]([NH2:21])=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][N:15]=[CH:16]2>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:1][CH2:2][C:3]([NH:21][C:20]1[C:11]([Cl:10])=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[N:15][CH:14]=[CH:13]2)=[O:5]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 300Chloroacetic AcidHCID 442770095-Chloroisoquinolin-6-amine

Product 1

HCID 59205709HCID 59205709, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To chloroacetic acid in DMF is added EDC, DMAP and 5-chloro-6-aminoisoquinoline. This mixture is stirred for 4 hours. The reaction is washed with NaHCO3(sat), extracted with EtOAc, dried (Na2SO4), filtered and evaporated. Column chromatography (SiO2, 5% MeOH/CH2Cl2) gives 2-chloro-N-(5-chloro-isoquinolin-6-yl) acetamide.

Workup

  1. washThe reaction is washed with NaHCO3(sat)
  2. extractionextracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9db0e8160b6e42e6a896303f0f8ab55d
Source dataset
uspto-grants-2011_10
Patent number
US08034943B2

Reaction notes

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