4-Bromo-3-chloro-2-methylaniline → 5-bromo-4-chloro-1H-indazole

HRID 2069569Notes

Reaction equation

HRID 2069569 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[C:3]=1[Cl:10].[N:11]([O-])=O.[Na+]>CC(O)=O.O>[Br:1][C:2]1[C:3]([Cl:10])=[C:4]2[C:5](=[CH:7][CH:8]=1)[NH:6][N:11]=[CH:9]2

Participants

5

Reactant 2

HCID 71719114-Bromo-3-chloro-2-methylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 457900305-bromo-4-chloro-1H-indazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 4-bromo-3-chloro-2-methylaniline (11 g, 49.9 mmol) in CH3CO2H (450 mL) was added NaNO2 (5.4 g, 78.3 mmol) in H2O (15 mL) at 10° C. The resulting mixture was stirred at room temperature for 30 minutes. Upon completion, the reaction mixture was diluted with H2O (500 mL) and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was triturated with petroleum ether affording the title compound (4.5 g) as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 13.60 (s, 1H), 8.15 (s, 1H), 7.62 (d, 1H), 7.52 (d, 1H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with petroleum ether affording the title compound (4.5 g) as yellow solid

Sources & evidence

ORD record
ord-5f3349ba6b2a49c7b56216e07d88c22a
Source dataset
uspto-grants-2012_10
Patent number
US08299112B2

Reaction notes

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