Sodium Chloride → [2-(4-Chloro-2-methylquinolin-8-yloxy)-ethyl]-carbamate tert-butyl ester

HRID 1966514Notes

Reaction equation

HRID 1966514 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:13]2[C:8](=[C:9]([OH:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([CH3:15])[CH:5]=1.[C:16]([NH:23][CH2:24][CH2:25]Br)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[Na+].[Cl-]>CC(N(C)C)=O>[C:19]([O:18][C:16](=[O:17])[NH:23][CH2:24][CH2:25][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[N:7]=[C:6]([CH3:15])[CH:5]=[C:4]2[Cl:3])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 59474799[2-(4-Chloro-2-methylquinolin-8-yloxy)-ethyl]-carbamate tert-butyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.6 g Sodium hydride, free of paraffin, was suspended in dimethyl acetamide (50 mL), then 4-chloro-2-methylquinoline-8-ol (1.6 g, 8.26 mmole) was added at RT and the mixture was stirred for 1 h. 2-(boc-amino)ethylbromide was added dropwise and the mixture was kept on stirring for 48 hrs. The content of the flask was poured into half concentrated NaCl solution and extracted with ethyl acetate. The organic phases were washed with water and saturated NaCl solution, dried and concentrated. Dimethyl acetamide was removed in vacuo and the residue was precipitated from isopropyl ether to give a light fawn solid (2.50 g, 90%).

Workup

  1. stirringon stirring for 48 hrs
  2. extractionextracted with ethyl acetate
  3. washThe organic phases were washed with water and saturated NaCl solution
  4. customdried
  5. concentrationconcentrated
  6. customDimethyl acetamide was removed in vacuo
  7. customthe residue was precipitated from isopropyl ether

Sources & evidence

ORD record
ord-2694007742144e748f073c8c5610192d
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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