Allyl bromide → Allyl-(5,6-dichloro-pyridin-3-yl)-(2,2-dimethoxy-ethyl)amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH:11]([O:14][CH3:15])[O:12][CH3:13])[CH:5]=[N:6][C:7]=1[Cl:8].[CH2:16](Br)[CH:17]=[CH2:18]>[Cl-].C[N+](CCCC)(CCCC)CCCC.C(OC)(C)(C)C.[OH-].[Na+]>[CH2:18]([N:9]([C:4]1[CH:5]=[N:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:10][CH:11]([O:14][CH3:15])[O:12][CH3:13])[CH:17]=[CH2:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
As shown in Scheme 2, the sequential treatment of 2-hydroxy-5-nitropyridine with potassium chlorate under heated conditions provides 3-chloro-2-hydroxy-5-nitropyridine which when further treated with phosphorous oxychloride under heated conditions provides 2,3-dichloro-5-nitropyridine. The nitro containing compound when treated to the reductive conditions of Raney-nickel and 40 PSI of hydrogen provides the amine which when further treated with glyoxal-1,2-dimethyl acetal in the presence of Raney-nickel under heated condition provides (5,6-dichloro-pyridin-3-yl)-(2,2-dimethoxy-ethyl)-amine. The amine when treated with allyl bromide and methyl tributyl ammonium chloride in a mixture of methyl tert-butyl ether and 50% aqueous sodium hydroxide provides allyl-(5,6-dichloro-pyridin-3-yl)-(2,2-dimethoxy-ethyl)amine (Compound 6E).
Sources & evidence
- ORD record
- ord-d478efc46daa4049bd756bddf927ac02
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902371B2
Reaction notes
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