Acetic Anhydride → 1-Methylethyl 5-(phenylmethoxy)-1H-indazole-3-carboxylate

HRID 1604630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604630
C([O-])(=O)C.[K+].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][C:8]=1[CH2:21][C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23].C(OC(=O)C)(=O)C.C(O[N:41]=O)CC(C)C>C1C=CC=CC=1>[CH2:14]([O:13][C:10]1[CH:9]=[C:8]2[C:7](=[CH:12][CH:11]=1)[NH:6][N:41]=[C:21]2[C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 21478799HCID 21478799, Verbindung

Produkt 1

HCID 196037391-Methylethyl 5-(phenylmethoxy)-1H-indazole-3-carboxylateAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of potassium acetate (1.34 g), isopropyl 2-amino-5-benzyloxyphenylacetate (3.9 g) and acetic anhydride (4.0 g) in benzene (40 ml) was stirred at 80° C. After 30 minutes, isopentylnitrite (2.3 g) was added dropwise to the mixture over 15 minutes and then the mixture was stirred at same temperature for 4 hours. After cooling, insoluble mass was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in isopropyl alcohol (30 ml) containing conc. sulphuric acid (0.5 ml) and the mixture was stirred at 80° C. for 3 hours. After cooling to room temperatures the resulting crystals were collected by filtration and washed with isopropyl ether to give isopropyl 5-benzyloxy-1H-indazole-3-carboxylate (2.4 g).

Aufarbeitung

  1. stirringthe mixture was stirred at same temperature for 4 hours
  2. temperatureAfter cooling
  3. filtrationinsoluble mass was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in isopropyl alcohol (30 ml)
  6. additioncontaining conc. sulphuric acid (0.5 ml)
  7. stirringthe mixture was stirred at 80° C. for 3 hours
  8. temperatureAfter cooling to room temperatures the resulting crystals
  9. filtrationwere collected by filtration
  10. washwashed with isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b5aca1c87310416d8e84518bd59f8223
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994378

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