Phosphorus oxychloride → 4-Chloro-3-nitro-1,5-naphthyridine

HRID 2090169Notes

Reaction equation

HRID 2090169 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

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526774HCID 178526774, compound

Product 1

HCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Referring to Scheme 1 (step 1), the present invention provides a method for preparing 4-chloro-3-nitro[1,5]naphthyridine. In some embodiments, the method includes: providing 3-nitro[1,5]naphthyridin-4-ol in a carrier that includes N,N-dimethylformamide (DMF); 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; and 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.

Sources & evidence

ORD record
ord-64d98f0fddfe4d54911d113495fb29d7
Source dataset
uspto-grants-2013_05
Patent number
US08436176B2

Reaction notes

Loading…