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Hydrochloric Acid → 4-[(2s,4r)-1-Acetyl-4-[(4-Chlorophenyl)amino]-2-Methyl-1,2,3,4-Tetrahydroquinolin-6-Yl]benzoic Acid

HRID 2041742
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2041742
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67205722Ethyl 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzoate

Produkt 1

HCID 529122224-[(2s,4r)-1-Acetyl-4-[(4-Chlorophenyl)amino]-2-Methyl-1,2,3,4-Tetrahydroquinolin-6-Yl]benzoic AcidAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

Ethyl 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzoate (for a preparation see Example 158) (5.41 g, 11.69 mmol) was dissolved in ethanol (100 mL) and the solution was treated with 2M NaOH aqueous solution (50 mL, 100 mmol). The resulting mixture was stirred at room temperature (air atmosphere) for approximately 2 h then most of the ethanol was removed in vacuo. The resulting yellow solution was diluted with water (resulting in the formation of an oily yellow precipitate). The aqueous phase was washed twice with DCM (which didn't dissolve the precipitate previously formed) then was acidified with a 2N hydrochloric acid aqueous solution to pH 1 and extracted twice with AcOEt. The combined AcOEt phases were washed with brine, dried using a hydrophobic frit and concentrated in vacuo. The residual yellow foam was triturated with Et2O over approximately 1 h. The resulting solid was isolated by filtration, washed with Et2O and air-dried to give 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzoic acid (4.41 g, 10.1 mmol, 87%) as a cream solid.

Aufarbeitung

  1. custommost of the ethanol was removed in vacuo
  2. additionThe resulting yellow solution was diluted with water (
  3. customresulting in the formation of an oily yellow precipitate)
  4. washThe aqueous phase was washed twice with DCM (which didn't
  5. dissolutiondissolve the precipitate
  6. custompreviously formed)
  7. extractionextracted twice with AcOEt
  8. washThe combined AcOEt phases were washed with brine
  9. customdried
  10. concentrationconcentrated in vacuo
  11. customThe residual yellow foam was triturated with Et2O over approximately 1 h
  12. customThe resulting solid was isolated by filtration
  13. washwashed with Et2O
  14. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-427e5440f33e4ee58e6720c09d021dca
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08580957B2

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