Phosphorus oxychloride → 4-Chloro-3-nitro-1,5-naphthyridine
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1O)=[N:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].P(Cl)(Cl)([Cl:17])=O>CN(C)C=O>[Cl:17][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][N:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In one aspect, the invention provides a method for making N4-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine. The method includes: providing 3-nitro[1,5]naphthyridin-4-ol in a carrier including N,N-dimethylformamide; combining the 3-nitro[1,5]naphthyridin-4-ol in the carrier with phosphorous oxychloride under conditions effective to form 4-chloro-3-nitro[1,5]naphthyridine; combining the mixture that includes the 4-chloro-3-nitro[1,5]naphthyridine with water under conditions effective to form solid 4-chloro-3-nitro[1,5]naphthyridine; separating at least a portion of the solid 4-chloro-3-nitro[1,5]naphthyridine from at least a portion of the mixture that includes the water; combining the separated solid 4-chloro-3-nitro[1,5]naphthyridine with a carrier that includes tetrahydrofuran; combining the 4-chloro-3-nitro[1,5]naphthyridine in the carrier with isobutylamine under conditions effective to form a mixture including N4-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine; combining the mixture that includes the N4-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine with water to form solid N4-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine; and separating at least a portion of solid N4-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine from at least a portion of the mixture that includes the water.
Sources & evidence
- ORD record
- ord-09d845938a4247d9816f762be9c91fbc
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436176B2
Reaction notes
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