Hydrochloric Acid → Dichloromethane methanol ammonium hydroxide

HRID 2044967Notes

Reaction equation

HRID 2044967 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[F:19])[C:8]([C@@H:20]([NH:22][C:23](C1C=CC=CC=1C(O)=O)=[O:24])[CH3:21])=[CH:7]2.C([OH:36])C.[ClH:37].C([O-])(O)=O.[Na+]>>[CH2:2]([Cl:1])[Cl:37].[CH3:23][OH:24].[NH4+:10].[OH-:36].[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[F:19])[C:8]([C@@H:20]([NH2:22])[CH3:21])=[CH:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 577078862-(((S)-1-(8-chloro-2-(2,3-difluorophenyl)quinolin-3-yl)ethyl)carbamoyl)benzoic acid

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 57707806(1S)-1-(8-chloro-2-(2,3-difluorophenyl)quinolin-3-yl)ethanamine

Procedure

To a suspension of 2-(((S)-1-(8-chloro-2-(2,3-difluorophenyl)quinolin-3-yl)ethyl)-carbamoyl)benzoic acid (0.2515 g, 0.5387 mmol) in ethanol (3.000 mL, 0.5387 mmol) was added 12 N HCl (1.500 mL, 18.00 mmol), and the mixture was stirred under reflux. After 12 h, the mixture was poured into ice water (50 mL). The mixture was neutralized with NaHCO3 and extracted with CH2Cl2 (50 mL×3). The combined organic layers were washed with brine (50 mL×3), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on a 40 g of Redi-Sep™ column using 0% to 50% gradient of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 over 14 min and then 50% isocratic of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 for 5 min as eluent to give (1S)-1-(8-chloro-2-(2,3-difluorophenyl)quinolin-3-yl)ethanamine as a light green syrup: LC-MS (ESI) m/z 319.1 [M+H]+.

Workup

  1. temperatureunder reflux
  2. extractionextracted with CH2Cl2 (50 mL×3)
  3. washThe combined organic layers were washed with brine (50 mL×3)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on a 40 g of Redi-Sep™ column
  8. customover 14 min

Sources & evidence

ORD record
ord-9843389ac4d1479cb3045d025437dbf8
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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