Hydrochloric Acid → 1-(1H-indazol-6-yl)ethan-1-one

HRID 1163422Notes

Reaction equation

HRID 1163422 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[CH3:9].[N:13]([O-])=O.[Na+].CC([O-])=O.[K+]>O.C1OCCOCCOCCOCCOCCOC1.C(Cl)Cl>[NH:2]1[C:3]2[C:8](=[CH:7][CH:6]=[C:5]([C:10](=[O:12])[CH3:11])[CH:4]=2)[CH:9]=[N:13]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3429141-(3-Amino-4-Methylphenyl)EthanoneHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 441192231-(1H-indazol-6-yl)ethan-1-oneYield 38.6%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Concentrated HCl (2 mL) was added to a mixture of 1-(3-amino-4-methylphenyl)ethanone (8.4 mmol) and NaBF4 (1.2 g, 11 mmol) in H2O (10 mL) and the solution was cooled to 0° C. A solution of NaNO2 (0.58 g, 8.4 mmol) in H2O (1.5 mL) was added dropwise and the mixture was stirred at 0° C. for 30 min. The solid that formed was collected by filtration and washed with H2O (5 mL) followed by Et2O (5 mL) and dried under a reduced pressure. CH2Cl2 (20 mL), KOAc (0.91 g, 9.3 mmol) and 18-crown-6 (50 mg, 0.2 mmol) was added to the solid and the mixture was stirred at room temperature for 4 h. H2O (20 mL) was added and the layers were separated. The organic layer was dried (MgSO4) and the solvent removed at reduced pressure to afford 1-(1H-indazol-6-yl)ethanone (0.52 g).

Workup

  1. customThe solid that formed
  2. filtrationwas collected by filtration
  3. washwashed with H2O (5 mL)
  4. customdried under a reduced pressure
  5. stirringthe mixture was stirred at room temperature for 4 h
  6. customthe layers were separated
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-1a8ef6f6466940249e02b91118e05bd2
Source dataset
uspto-grants-2010_10
Patent number
US07820821B2

Reaction notes

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