Hydrazine hydrate (1:1) → 8-(3-Chloro-propoxy)-5,6-dihydro-2H-benzo[h]cinnolin-3-one

HRID 2042629

Reaktionsgleichung

Reaktionsgleichung von HRID 2042629
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=O)[CH2:11][CH2:10][CH2:9]2.O.[C:18]([OH:22])(=O)[CH:19]=O.O.[NH2:24][NH2:25]>C(O)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:12]3[C:11](=[CH:19][C:18](=[O:22])[NH:24][N:25]=3)[CH2:10][CH2:9][C:8]=2[CH:7]=1

Komponenten

5

Edukt 3

HCID 24654Hydrazine hydrate (1:1)HCID 15620607Glyoxylic acid, monohydrateHCID 220232326-(3-Chloro-propoxy)-3,4-dihydro-2H-naphthalen-1-one

Produkt 1

HCID 596519418-(3-Chloro-propoxy)-5,6-dihydro-2H-benzo[h]cinnolin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

In a 100 mL round bottom flask, 6-(3-chloro-propoxy)-3,4-dihydro-2H-naphthalen-1-one (1 g, 4.2 mmol), and glyoxylic acid monohydrate (387 mg, 4.2 mmol), in acetic acid (10 mL) was heated to reflux 6 h. The reaction was cooled and hydrazine monohydrate (0.41 mL, 8.4 mmol) was added and the reaction was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. The slurry was partitioned between methylene chloride and water, separated, dried over MgSO4. Purification with silica gel chromatography eluting with methylene chloride/methanol (95:5) produced 620 mg (51%). MS m/z 291 (M+H).

Aufarbeitung

  1. temperatureto reflux 6 h
  2. temperatureThe reaction was cooled
  3. temperaturethe reaction was heated
  4. temperatureto reflux 14 h
  5. temperatureThe reaction was cooled
  6. concentrationthe solvent concentrated under vacuum
  7. customThe slurry was partitioned between methylene chloride and water
  8. customseparated
  9. dry with materialdried over MgSO4
  10. customPurification with silica gel chromatography
  11. washeluting with methylene chloride/methanol (95:5)
  12. customproduced 620 mg (51%)

Quellen und Nachweise

ORD-Eintrag
ord-dd0264ce40e44ef0bd7ed89a042333c5
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586588B2

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