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

HRID 567813Notes

Reaction equation

HRID 567813 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-4ae1adef5d8d4b6eb5cbd8c118b75bfe
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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