Ethanol → Dichloromethane methanol ammonium hydroxide

HRID 2044975Notes

Reaction equation

HRID 2044975 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH:18]([N:20]2[C:28](=[O:29])C3C(=CC=CC=3)C2=O)[CH3:19])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([F:31])=[CH:13][CH:14]=2)[N:9]=1.C([OH:34])C.O.NN.[CH2:38]([Cl:40])[Cl:39]>>[CH2:38]([Cl:40])[Cl:39].[CH3:28][OH:29].[NH4+:9].[OH-:34].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH:18]([NH2:20])[CH3:19])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([F:31])=[CH:13][CH:14]=2)[N:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 57707857HCID 57707857, compound

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 57707890HCID 57707890, compound

Procedure

To a suspension of 2-(1-(2-(2-chlorophenyl)-7-fluoroquinolin-3-yl)ethyl)-isoindoline-1,3-dione (impure) (0.9331 g, 2.166 mmol) in ethanol (43.31 mL, 2.166 mmol) was added hydrazine hydrate (1.349 mL, 43.31 mmol), and the mixture was stirred under reflux. After 2.5 h, the mixture was cooled to room temperature. The mixture was diluted with CH2Cl2 (50 mL), filtered to removed the precipitated byproduct, and washed the filtered solid with CH2Cl2 (50 mL). The filtrate containing the desired product was concentrated under reduced pressure. The residue was purified by column chromatography on a 80 g of Redi-Sep™ column using 0% to 50% gradient of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 over 25 min, and then 50% isocratic of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 for 5 min as eluent to give 1-(2-(2-chlorophenyl)-7-fluoroquinolin-3-yl)-ethanamine as a yellow syrup: LC-MS (ESI) m/z 301.1 [M+H]+.

Workup

  1. temperatureunder reflux
  2. filtrationfiltered
  3. customto removed the precipitated byproduct
  4. washwashed the filtered solid with CH2Cl2 (50 mL)
  5. additionThe filtrate containing the desired product
  6. concentrationwas concentrated under reduced pressure
  7. customThe residue was purified by column chromatography on a 80 g of Redi-Sep™ column
  8. customover 25 min

Sources & evidence

ORD record
ord-4cf78cc3b0494f8b957af992944927d6
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

Loading…