Hydrochloric Acid → HCID 69001756, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1/[CH:10]=[CH:11]/[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][N:13]=1)([O-])=O.[Sn].Cl.[OH-].[Na+]>C(O)C>[NH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](/[CH:11]=[CH:10]/[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH2:1])=[N:13]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
(E)-3-[2-(2-nitrophenyl)vinyl]-1H-indazole (4 g, 15.08 mmol) obtained in Example 1 was dissolved in ethanol (68 mL), and the solution was added with tin (3.85 g, 32.40 mmol) and concentrated hydrochloric acid (34 mL, 400 mmol) under ice-cooling, followed by stirring at 40° C. for 3 hours. To the reaction mixture, 6 mol/L aqueous sodium hydroxide solution was added to neutralize the mixture under ice-cooling. Then the mixture was filtered. The filtrate was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then the solvent was evaporated under reduced pressure. The residue was triturated in ethyl acetate to obtain Compound 2 (2.98 g, 84%).
Workup
- temperaturecooling
- temperaturecooling
- filtrationThen the mixture was filtered
- additionThe filtrate was added with saturated aqueous sodium hydrogencarbonate solution
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was triturated in ethyl acetate
Sources & evidence
- ORD record
- ord-1945d9d85449493e9e5d16ae1e177062
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07605272B2
Reaction notes
Loading…