4-Bromo-2-ethylaniline → HCID 178434225, compound

HRID 1403381Notes

Reaction equation

HRID 1403381 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH2:9][CH3:10])[CH:3]=1.[N:11]([O-])=O.[Na+]>CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][N:11]=[C:9]2[CH3:10]

Participants

4

Reactant 2

HCID 28012834-Bromo-2-ethylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 178434225HCID 178434225, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-bromo-2-ethylbenzenamine (1.5 g, 7.50 mmol) in AcOH (20 mL) was added NaNO2 (570 mg, 8.14 mmol). After stirring for 2.5 h at room temperature, the resulting mixture was concentrated under reduced pressure to afford a residue, which was purified by a silica gel column with 1% methanol in dichloromethane to afford 5-bromo-3-methyl-1H-indazole as a light red solid (700 mg, 44%).

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. customto afford a residue, which
  3. customwas purified by a silica gel column with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-a0b868519d7843438737718cfa927b0d
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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