Water → 7-chloro-1-(1,3-dioxolan-2-ylmethyl)-1,8-naphthyridin-2(1H)-one

HRID 385508ノート

反応式

HRID 385508 の反応式
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH:21]1[O:25][CH2:24][CH2:23][O:22]1.O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[N:9]2[CH2:20][CH:21]2[O:25][CH2:24][CH2:23][O:22]2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium Carbonate2 回HCID 780681,3-Dioxolane, 2-(bromomethyl)-2 回HCID 133023227-Chloro-1,8-naphthyridin-2-ol

生成物 1

HCID 578152377-chloro-1-(1,3-dioxolan-2-ylmethyl)-1,8-naphthyridin-2(1H)-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3.2 g of 7-chloro-1,8-naphthyridin-2(1H)-one in 32 mL of N,N-dimethylformamide, 3.7 g of potassium carbonate was added, and the mixture was stirred at 50 to 60 C.° for 23 minutes, and then, thereto was added 2.2 mL of 2-bromomethyl-1,3-dioxolan, and the mixture was stirred at 60 to 78° C. for 25 minutes. Thereto were added 16 mL of N,N-dimethylformamide and 1.1 mL of 2-bromomethyl-1,3-dioxolan, the mixture was stirred at 90 to 95° C. for 2 hours 15 minutes, 3.7 g of potassium carbonate was added thereto, and the mixture was stirred for 20 minutes. The reaction mixture was cooled to room temperature, water and ethyl acetate were then added thereto, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of hexane:ethyl acetate=1:1 to obtain 3.6 g of 7-chloro-1-(1,3-dioxolan-2-ylmethyl)-1,8-naphthyridin-2(1H)-one as a yellow solid.

後処理

  1. stirringthe mixture was stirred at 60 to 78° C. for 25 minutes
  2. stirringthe mixture was stirred at 90 to 95° C. for 2 hours 15 minutes
  3. stirringthe mixture was stirred for 20 minutes
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resultant residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-e733378c1f124fd693392730bff9e3e5
出典データセット
uspto-grants-2013_02
特許番号
US08367831B2

反応ノート

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