Nitric Acid → 2,3-Dihydro-1'-acetyl-5-nitrospiro[benzofuran-2,4'-piperidine]

HRID 261505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 261505
[N+:1]([O-:4])(O)=[O:2].[C:5]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:10][CH2:9]1)(=[O:7])[CH3:6].O>C(O)(=O)C>[C:5]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:17][C:16]3[CH:18]=[C:19]([N+:1]([O-:4])=[O:2])[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:10][CH2:9]1)(=[O:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 962WaterHCID 127332342,3-Dihydro-1'-acetylspiro[benzofuran-2,4'-piperidine]

Produkt 1

HCID 127332352,3-Dihydro-1'-acetyl-5-nitrospiro[benzofuran-2,4'-piperidine]

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3.8 g of nitric acid (sp gr 1.42) in 30 ml of glacial acetic acid are added dropwise to a stirred solution of 4.7 g of 2,3-dihydro-1'-acetylspiro[benzofuran-2,4'-piperidine], Example 16, in 65 ml of glacial acetic acid. After total addition, the reaction mixture is slowly heated to 100° C. over a 2 hour span and then cooled and poured into 500 ml of water. The diluted mixture is extracted with chloroform and the chloroform extracts are washed sequentially with a saturated sodium bicarbonate solution, a saturated sodium chloride solution and then dried. The chloroform is removed under reduced pressure. The residue is triturated with ether, causing an orange precipitate which is collected and recrystallized first from an ethyl alcohol-ether mixture and then from ethyl alcohol to provide the product, 2,3-dihydro-1'-acetyl-5-nitrospiro[benzofuran-2,4'-piperidine], mp 149°-150° C.

Aufarbeitung

  1. additionAfter total addition
  2. temperaturecooled
  3. extractionThe diluted mixture is extracted with chloroform
  4. washthe chloroform extracts are washed sequentially with a saturated sodium bicarbonate solution
  5. dry with materiala saturated sodium chloride solution and then dried
  6. customThe chloroform is removed under reduced pressure
  7. customThe residue is triturated with ether
  8. customis collected
  9. customrecrystallized first from an ethyl alcohol-ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-0fe34590c02f40798db12b495e8c8341
Quelldatensatz
uspto-grants-1979_08
Patentnummer
US04166119

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