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

HRID 40365

反応式

HRID 40365 の反応式
[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>ClCCl>[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

参加物

5

反応物 3

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

生成物 1

HCID 1357435768-Chloro-1,5-naphthyridin-3-ol収率 56.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

A pressure-resistant vial was charged with 8-chloro-3-methoxy-1,5-naphthyridine (2.5 g, 12.8 mmol), boron tribromide (13.4 mL, 141.3 mmol) and dichloroethane (0.6M, 21.4 mL). Vessel sealed and mixture stirred at 60° C. for 16 hrs. Next day the reaction mixture was chilled in ice bath and diluted with dichloromethane (200 mL). This was allowed to sit under nitrogen system until all fuming ceased. The resulting yellow solid material was then filtered and dried under high vacuum. This was suspended in 40% (90:10:1 DCM/MeOH/NH4OH)/DCM and purified in this system by ISCO silica gel chromatography (80 g) afford 8-chloro-1,5-naphthyridin-3-ol (1.3 g, 56% yield). MS [M+H]=181.2. Calc'd for C8H5ClN2O=180.59.

後処理

  1. customVessel sealed
  2. temperatureNext day the reaction mixture was chilled in ice bath
  3. filtrationThe resulting yellow solid material was then filtered
  4. customdried under high vacuum
  5. custompurified in this system by ISCO silica gel chromatography (80 g)

出典と根拠

ORDレコード
ord-6f4a85c5f5fa432aa161793f77ea5d01
出典データセット
uspto-grants-2013_09
特許番号
US08524900B2

関連ノート

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