Stannous Chloride → 5-Methyl-3-phenyl-1H-indazole

HRID 2183098Notes

Reaction equation

HRID 2183098 reaction equation
[C:1]1([C:7]([C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=2[NH2:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17]([O-])=O.[Na+].Cl[Sn]Cl>Cl.O>[CH3:15][C:13]1[CH:14]=[C:9]2[C:10](=[CH:11][CH:12]=1)[NH:16][N:17]=[C:7]2[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 873352-Amino-5-methylbenzophenoneHCID 23668193Sodium Nitrite

Product 1

HCID 6104125-Methyl-3-phenyl-1H-indazoleYield 80.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 2-amino-5-methylphenyl phenyl ketone (2.0 g, 9.5 mmol) in HCl (45 mL of a 6M solution) at 0° C. was added sodium nitrite (NaNO2) (719 mg, 10.4 mmol) in water (2 mL). The reaction was stirred for 30 min when the homogeneous solution was added dropwise to a solution of SnCl2 (5.88, 26 mmol) in concentrated HCl (15 mL) at room temperature. The reaction was stirred for 30 min when it was filtered. The solid was then taken up in ethyl acetate (80 mL) and saturated sodium bicarbonate (80 mL). The suspension was then filtered and the ethyl acetate layer dried (Na2SO4) and concentrated to give the product (1.59 g, 80% yield). (1H NMR (DMSO-d6) δ 7.96 (d, 2H), 7.85 (br s, 1H), 7.54-7.46 (m, 3H), 7.39 (t, 1H), 7.24 (d, 1H), 2.45 (s, 3H); ES-MS (m/z) 209 [M+1]+.

Workup

  1. stirringThe reaction was stirred for 30 min when it
  2. filtrationwas filtered
  3. filtrationThe suspension was then filtered
  4. dry with materialthe ethyl acetate layer dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-928f0a7d5ff54bdc82b98b42e63f5539
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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