Sulfuric Acid → HCID 69036629, compound

HRID 1930372Notes

Reaction equation

HRID 1930372 reaction equation
OS(O)(=O)=O.[N+:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][N:10]=1)([O-:8])=[O:7]>CC(O)(C)C.CCOC(C)=O>[C:17]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([N+:6]([O-:8])=[O:7])=[N:10]1)([CH3:12])([CH3:9])[CH3:16]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 178526903HCID 178526903, compound

Product 1

HCID 69036629HCID 69036629, compoundYield 147.7%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cone. H2SO4 (2 mL) was added to a suspension of 3-nitro-1 H-indazole (3.4 g, 21 mmol) in 2-methyl-propan-2-ol (30 mL) and the resulting mixture was heated to 180° C. in a steel bomb. The reaction mixture was cooled to RT and diluted with EtOAc. The organic phase was washed with brine, dried (MgSO4) and concentrated to give 1-tert-butyl-3-nitro-1 H-indazole (3.4 g, 76%). 1H NMR (400 MHz, DMSO-d6): δ 8.18-8.15 (m, 2 H), 7.59-7.49 (m, 2 H), 1.76 (s, 9 H).

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-582fd19f0c75492091508923c621cc11
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

Loading…