Methyl 3-amino-4-methylbenzoate → methyl 1H-indazole-6-carboxylate

HRID 508200

Reaktionsgleichung

Reaktionsgleichung von HRID 508200
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[N:13]([O-])=O.[Na+]>CC(O)=O.O>[NH:1]1[C:2]2[C:11](=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)[CH:12]=[N:13]1

Komponenten

5

Edukt 2

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 286535methyl 1H-indazole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-amino-4-methylbenzoate D-1 (5.0 g, 30 mmol) in AcOH (140 mL) at 0° C. was added a solution of sodium nitrite (2.1 g, 30 mmol) in H2O (3.5 mL). After addition, the mixture was stirred at rt for 24 h. Then half of the solvent was removed under reduced pressure and the resulting mixture was diluted with H2O, and extracted with EtOAc. The combined organics were washed H2O and brine, and concentrated to give the title compound. LCMS (ESI) calc'd for C9H9N2O2 [M+H]+: 177. found 177.

Aufarbeitung

  1. additionAfter addition
  2. customThen half of the solvent was removed under reduced pressure
  3. additionthe resulting mixture was diluted with H2O
  4. extractionextracted with EtOAc
  5. washThe combined organics were washed H2O and brine
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5b4f708b0c6244d7a112f0e8c44dfad3
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09095583B2

Verknüpfte Notizen

Wird geladen…