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O-Methylhydroxylamine hydrochloride → 6-Chloro-2-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid

HRID 750180
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 750180
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.[CH3:23][O:24][NH2:25].C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:25]([O:24][CH3:23])[C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 103800926-chloro-4-phenylisocoumarin-3-carboxylic AcidHCID 10942334Sodium Methoxide

Produkt 1

HCID 230609396-Chloro-2-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

6-Chloro-1-oxo-4-phenyl-1H-isochromen-3-carboxylic acid (150 mg) was dissolved in methanol (3.0 ml) and O-methylhydroxylamine hydrochloride (420 mg) and sodium methoxide (270 mg) were added. The mixture was stirred at room temperature for 12 hrs. and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and 1N hydrochloric acid, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure to dryness. Then, 4N hydrochloric acid ethyl acetate solution (3 ml) was added to the residue and the mixture was stirred at room temperature for 12 hrs. Water was added to wash the reaction mixture, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 6-chloro-2-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid.

Aufarbeitung

  1. concentrationand concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure to dryness
  5. additionThen, 4N hydrochloric acid ethyl acetate solution (3 ml) was added to the residue
  6. stirringthe mixture was stirred at room temperature for 12 hrs
  7. additionWater was added
  8. washto wash the reaction mixture
  9. dry with materialthe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e1fb45fe558468294b5dc3035649200
Quelldatensatz
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07402595B2

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