HCID 131736104, compound → HCID 82627609, compound
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([O:12][CH3:13])[C:3]=1[CH:4]=[N:5]O>CC(O)=O.[Zn]>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([O:12][CH3:13])[C:3]=1[CH2:4][NH2:5]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A suspension of 2,4-dichloro-6-methoxybenzaldehyde oxime (2.24 mmol) in 3 mL AcOH was cooled to 0° C. and zinc dust (8.53 mmol) was added. The reaction mixture was stirred at RT for 2 h. It was filtered over a pad of celite and washed with EtOAc and MeOH. The filtrate was conc. and redissolved in water (pH 4 with 2N HCl solution). It was washed once with EtOAc, the ageous phase was basified with 1M NaOH solution, extracted 3 times with EtOAc and DCM. The comb. org. layers were dried over MgSO4 and conc. in vacuo to give the desired product as yellow solid.
Workup
- filtrationIt was filtered over a pad of celite
- washwashed with EtOAc and MeOH
- dissolutionredissolved in water (pH 4 with 2N HCl solution)
- washIt was washed once with EtOAc
- extractionextracted 3 times with EtOAc and DCM
- dry with materiallayers were dried over MgSO4 and conc. in vacuo
Sources & evidence
- ORD record
- ord-59c886d11b7f480bb9774ceb92f1d49a
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388197B2
Reaction notes
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