Ammonia → HCID 59702374, compound

HRID 902557Notes

Reaction equation

HRID 902557 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[C:13](=[C:14]([CH2:19]O)[N:15]([CH3:18])[N:16]=2)[CH:12]=[CH:11][CH:10]=1.[NH3:21].CC(O)C.[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[C:13](=[C:14]([C:19]#[N:21])[N:15]([CH3:18])[N:16]=2)[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 3776IsopropanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 59702371HCID 59702371, compound

Product 1

HCID 59702374HCID 59702374, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [7-(2,4-dichloro-phenyl)-2-methyl-2H-indazol-3-yl]-methanol from step 2 (0.153 g) in 2 mL of THF was added a 2 M ammonia in IPA solution (1.0 mL, 2.0 mmol), MgSO4 (0.910 g, 7.56 mmol), and 85% activated MnO2 (0.771 g, 7.54 mmol). The dark mixture was stirred for 2 d, then filtered thru CELITE® 521 (rinsing with dichloromethane) and concentrated to a yellow solid. Column chromatography (0→10% EtOAc/hexanes) afforded 7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole-3-carbonitrile (20: R3=2,4-dichlorophenyl; 0.058 g; 39%; m.p. 137-139) as a white solid:

Workup

  1. filtrationfiltered thru
  2. washCELITE® 521 (rinsing with dichloromethane)
  3. concentrationconcentrated to a yellow solid

Sources & evidence

ORD record
ord-8bab27a767874f968f7c6b7c1ec27821
Source dataset
uspto-grants-2008_04
Patent number
US07365211B2

Reaction notes

Loading…