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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 572348
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 572348
[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]
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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 Intermediate 17) (5.41 g, 11.69 mmol) was dissolved in ethanol (100 mL) and the solution was treated with aqueous NaOH solution (2M, 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 hydrochloric acid (2N) to pH 1 and extracted with EtOAc (×2). The combined EtOAc phases were washed with brine, dried (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. LCMS (HpH), Retention time 1.08 min, [M−H]−=433

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 with EtOAc (×2)
  8. washThe combined EtOAc phases were washed with brine
  9. customdried (hydrophobic frit)
  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-d5041e4c247545a584f6b924bdc877ec
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029395B2

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