Ammonium Hydroxide → 8-[3-(2-Methyl-pyrrolidin-1-yl)-propoxy]-4,4a,5,6-tetrahydro-2H-benzo[h]cinnolin-3-one

HRID 2042632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042632
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17](=O)[CH2:16][CH2:15][CH2:14]2.O.[C:23]([OH:27])(=O)[CH:24]=O.[NH4+:28].[OH-].O.[NH2:31]N.C([O-])(O)=O.[Na+]>C(O)(=O)C.O.[Zn]>[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][C:18]2[C:17]3[CH:16]([CH2:24][C:23](=[O:27])[NH:28][N:31]=3)[CH2:15][CH2:14][C:13]=2[CH:12]=1

Komponenten

9

Edukt 5

HCID 14923Ammonium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 15620607Glyoxylic acid, monohydrateHCID 596519636-[3-((R)-2-Methyl-pyrrolidin-1-yl)-propoxy]-3,4-dihydro-2H-naphthalen-1-one

Produkt 1

HCID 685965348-[3-(2-Methyl-pyrrolidin-1-yl)-propoxy]-4,4a,5,6-tetrahydro-2H-benzo[h]cinnolin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

In a 250 mL round bottom flask, 6-[3-((R)-2-Methyl-pyrrolidin-1-yl)-propoxy]-3,4-dihydro-2H-naphthalen-1-one (3.0 g, 9.3 mmol), and glyoxylic acid monohydrate (1.28 g, 13.9 mmol), in acetic acid (60 mL) was heated to reflux 3 h. The reaction was cooled and zinc dust (1.21 g, 18.5 mmol) was added and the reaction was heated to reflux 14 h. The reaction was cooled and diluted with water (120 mL). The mixture was basified to pH 8 with NH4OH and then hydrazine monohydrate (0.93 mL, 18.5 mmol) was added. The reaction was heated to reflux 2 h. The reaction was cooled and re-basified with NaHCO3, then extracted with methylene chloride three times. The organics were dried over MgSO4, then ethereal HCL was added. The solvents were removed under vacuum and the product was crystallized with MeOH/ether to produce 1.16 g (33%). Mp 193-195° C. MS m/z 342 (M+H).

Aufarbeitung

  1. temperatureto reflux 3 h
  2. temperatureThe reaction was cooled
  3. temperaturethe reaction was heated
  4. temperatureto reflux 14 h
  5. temperatureThe reaction was cooled
  6. temperatureThe reaction was heated
  7. temperatureto reflux 2 h
  8. extractionextracted with methylene chloride three times
  9. dry with materialThe organics were dried over MgSO4
  10. additionethereal HCL was added
  11. customThe solvents were removed under vacuum
  12. customthe product was crystallized with MeOH/ether
  13. customto produce 1.16 g (33%)

Quellen und Nachweise

ORD-Eintrag
ord-3496efe6f12145b9b8ad37bfa7b70dbf
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586588B2

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