1,1-Dichloroethane → 8-Chloro-1,5-naphthyridin-3-ol

HRID 1042918Notes

Reaction equation

HRID 1042918 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12]C)=[CH:7]2.B(Br)(Br)Br.ClC(Cl)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([OH:12])=[CH:7]2

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 25134Boron tribromideHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

Product 1

HCID 1357435768-Chloro-1,5-naphthyridin-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A pressure-resistant vial was charged with 8-chloro-3-methoxy-1,5-naphthyridine (1200 mg, 6166 μmol), boron tribromide (6412 μl, 67825 μmol) and dichloroethane (10277 μl, 6166 μmol). The vessel was sealed and the mixture was stirred at 60° C. for 16 h. The reaction mixture was carefully diluted with DCM, and the solids were filtered. The crude material was purified by silica gel chromatography with 40-70% (90:10:1 DCM/MeOH/NH4OH)/DCM to afford 8-chloro-1,5-naphthyridin-3-ol. MS: [M+H]=181.

Workup

  1. customThe vessel was sealed
  2. filtrationthe solids were filtered
  3. customThe crude material was purified by silica gel chromatography with 40-70% (90:10:1 DCM/MeOH/NH4OH)/DCM

Sources & evidence

ORD record
ord-3b239abd4cd94f709a74e74471dc02dc
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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