1,2-Dichloroethane → 2-chloro-N-(isoquinolin-6-yl)acetamide

HRID 1409661

Reaction equation

HRID 1409661 reaction equation
[Cl:1][CH2:2][C:3]([OH:5])=O.C(Cl)CCl.[NH2:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[N:16][CH:15]=[CH:14]2>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:1][CH2:2][C:3]([NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[N:16][CH:15]=[CH:14]2)=[O:5]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 300Chloroacetic AcidHCID 5889916-Aminoisoquinoline

Product 1

HCID 249995012-chloro-N-(isoquinolin-6-yl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To chloroacetic acid in DMF was added EDC, DMAP and 6-aminoisoquinoline. This mixture was stirred for 4 hours. The reaction was washed with NaHCO3(sat), extracted with EtOAc, dried (Na2SO4), filtered and evaporated. Column chromatography (SiO2, 5% MeOH/CH2Cl2) gave 2-chloro-N-(isoquinolin-6-yl)acetamide (E1).

Workup

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

Sources & evidence

ORD record
ord-aa7cb571d2084709a5a28babe1feb6b6
Source dataset
uspto-grants-2014_12
Patent number
US08921392B2

Linked notes

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