Nitric Acid → HCID 131716240, Verbindung

HRID 329746

Reaktionsgleichung

Reaktionsgleichung von HRID 329746
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH:17]2[CH:22]3[CH2:23][CH2:24]N(CC3)C2)=[O:15])[C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[CH:13]=1.[N+:25]([O-:28])(O)=[O:26]>S(=O)(=O)(O)O>[OH2:10].[ClH:1].[Cl:1][C:2]1[C:3]([N+:25]([O-:28])=[O:26])=[C:4]([C:14]([NH:16][CH:17]2[CH2:22][CH:23]3[CH2:24][CH2:8][N:7]2[CH2:6][CH2:5]3)=[O:15])[C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[CH:13]=1.[Cl:1][C:2]1[C:3]([N+:25]([O-:28])=[O:26])=[C:4]([C:14]([NH:16][CH:17]2[CH2:22][CH:23]3[CH2:24][CH2:17][N:16]2[CH2:14][CH2:4]3)=[O:15])[C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[CH:13]=1.[ClH:1]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 2264Azasetron

Produkt 1

HCID 131716240HCID 131716240, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Versuchsvorschrift

A solution of 10.5 g of 6-chloro-3,4-dihydro-4-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide in 50 ml of concentrated sulfuric acid is cooled to a temperature below 0° C., and a mixture of 1.5 ml of fuming nitric acid (d 1.50) and 1.5 ml of concentrated sulfuric acid is added dropwise thereto at a temperature below 5° C. The resultant mixture is stirred under ice-cooling for 1.5 hours and poured into ice-cold water. After extracting with ethyl acetate, the extract is washed with water and dried over magnesium sulfate. The solvent is distilled off followed by recrystallizing from ethanol and treating with ethanolic hydrochloric acid to give 6-chloro-3,4-dihydro-4-methyl-7-nitro-3-oxo-N-(quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride hemihydrate. The melting point and NMR spectra are identical with those of the compound as prepared in Example 30(1).

Aufarbeitung

  1. additionis added dropwise
  2. customat a temperature below 5° C
  3. temperaturecooling for 1.5 hours
  4. additionpoured into ice-cold water
  5. extractionAfter extracting with ethyl acetate
  6. washthe extract is washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent is distilled off
  9. customby recrystallizing from ethanol
  10. additiontreating with ethanolic hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-ef1278346bae4fbfafd5f107b4b3da05
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892872

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