HCID 86665739, compound → HCID 86665740, compound
Reaction equation
[Br:1][C:2]([Br:16])=[CH:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[CH:7]=[CH:6][C:5]=1[N+:13]([O-])=O>CO.[Pt]>[Br:1][C:2]([Br:16])=[CH:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[CH:7]=[CH:6][C:5]=1[NH2:13]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of 2-(2,2-dibromovinyl)-4-ethoxynitrobenzene (200 mg) in methanol (3 mL) was added 1% platinum on activated carbon (vanadium doped, 50% hydrous, 27.5 mg) at room temperature, and the mixture was stirred for six and a half hours under a hydrogen atmosphere. 1% Platinum on activated carbon (vanadium doped, 50% hydrous, 27.5 mg) was added, and the mixture was stirred for additional one hour under a hydrogen atmosphere. The reaction mixture was filtered through celite (registered trademark) and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (155 mg).
Workup
- stirringthe mixture was stirred for additional one hour under a hydrogen atmosphere
- filtrationThe reaction mixture was filtered through celite (registered trademark)
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)
Sources & evidence
- ORD record
- ord-3855f8ad0fc2444d8f4f00e6390939e0
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680120B2
Reaction notes
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