4-Amino-2,5-dimethylbenzonitrile → 6-Methyl-1H-indazole-5-carbonitrile

HRID 567813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 567813
[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:11])[CH:3]=1.[N:12]([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:11][C:4]1[CH:3]=[C:2]2[C:9]([CH:10]=[N:12][NH:1]2)=[CH:8][C:5]=1[C:6]#[N:7]

Komponenten

5

Edukt 2

HCID 184708764-Amino-2,5-dimethylbenzonitrileHCID 23668193Sodium Nitrite

Produkt 1

HCID 184708486-Methyl-1H-indazole-5-carbonitrileAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4-amino-2,5-dimethylbenzonitrile (preparation 31) (111 mg, 0.76 mmol) in acetic acid (5 ml) was treated with a solution of sodium nitrite (53 mg, 0.76 mmol) in water (1 ml). The resultant mixture was stirred at room temperature for 10 mins then left to stand for 48 hrs. The solvent was removed by evaporation and the residue purified by chromatography (SiO2, eluting with 50:50 hexane: ethyl acetate) to give the desired product (25 mg, 21%). 1H NMR (CD3OD) δ 2.60 (s, 3H), 7.50 (s, 1H), 8.15 (s, 1H), 8.20 (s, 1H). LRMS m/z=158.1 (M+1)+.

Aufarbeitung

  1. waitthen left
  2. customThe solvent was removed by evaporation
  3. customthe residue purified by chromatography (SiO2, eluting with 50:50 hexane: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4ae1adef5d8d4b6eb5cbd8c118b75bfe
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180627B2

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