HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → 6-Chloro-2-morpholin-4-yl-4-phenyl-quinoline-3-carboxylic acid

HRID 1497058
Notes
Print preview

Reaction equation

HRID 1497058 reaction equation
C([O:3][C:4]([C:6]1[C:7]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)=[O:5])C.[OH-].[Na+]>C(O)C.O>[Cl:22][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)[C:6]([C:4]([OH:5])=[O:3])=[C:15]2[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 866829316-Chloro-2-morpholin-4-yl-4-phenyl-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 715562896-Chloro-2-morpholin-4-yl-4-phenyl-quinoline-3-carboxylic acidYield 15.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 6-chloro-2-morpholin-4-yl-4-phenyl-quinoline-3-carboxylic acid ethyl ester (100 mg, 0.25 mmol) in ethanol (10 ml) was added 1N NaOH (1.26 ml, 1.26 mmol) solution at RT. The reaction mixture was refluxed for 24 h. The volatiles were removed under vacuum to afford a crude residue which was diluted with water. The aqueous layer was washed with ethyl acetate to remove non-polar impurities and then the pH was adjusted to 4-3 with 10% citric acid under cooling. Then the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to give a crude residue which was purified via Prep-HPLC followed by Prep-TLC to obtain pure 6-chloro-2-morpholin-4-yl-4-phenyl-quinoline-3-carboxylic acid as pale yellow solid (14 mg, 15%). LC-MS: 369 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. customThe volatiles were removed under vacuum
  3. customto afford a crude residue which
  4. washThe aqueous layer was washed with ethyl acetate
  5. customto remove non-polar impurities
  6. temperatureunder cooling
  7. extractionThen the aqueous layer was extracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customto give a crude residue which
  12. customwas purified via Prep-HPLC

Sources & evidence

ORD record
ord-171c08f15b404955bf1b4d8e23d105f1
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09199938B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes