Ethyl 4-methyl-3-nitrobenzoate → Ethyl 1H-indazole-6-carboxylate

HRID 258261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 258261
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-])=O.[N:16]([O-])=O.[Na+]>C(O)(=O)C.O>[NH:13]1[C:3]2[C:2](=[CH:12][CH:11]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=2)[CH:1]=[N:16]1

Komponenten

5

Edukt 2

HCID 14945864Ethyl 4-methyl-3-nitrobenzoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 19737203Ethyl 1H-indazole-6-carboxylateAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Ethyl 4-methyl-3-nitrobenzoate (105 g) was dissolved in glacial acetic acid (4 1), followed by stirring. To the solution, a solution of sodium nitrite (32 g) in water (80 ml) was added at once at a temperature of 10° C. to 15° C., and the resultant mixture was stirred at room temperature for 3 days. After completion of the reaction, the reaction mixture was evaporated under reduced pressure to remove acetic acid. Water was added to the residue, and the precipitated crystals were collected by filtration. The collected crystals were washed with water and dried. The obtained crystals was further washed with methanol and diethyl ether, and dried to give ethyl indazol-6-yl carboxylate (90 g), m.p. 125°-126° C.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe reaction mixture was evaporated under reduced pressure
  3. customto remove acetic acid
  4. additionWater was added to the residue
  5. filtrationthe precipitated crystals were collected by filtration
  6. washThe collected crystals were washed with water
  7. customdried
  8. washThe obtained crystals was further washed with methanol and diethyl ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4e1966ecea50402686aeb40aa4016c67
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05266556

Notizen zur Reaktion

Wird geladen…