Methanol → 1-(3-Bromo-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

HRID 351729ノート

反応式

HRID 351729 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]([C:19]([O:21]CC)=[O:20])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.CO.[OH-].[Na+]>O1CCCC1.O.Cl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]([C:19]([OH:21])=[O:20])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11057804Ethyl 1-(3-bromophenyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

生成物 1

HCID 223919781-(3-Bromo-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of ethyl 1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate from Step 2 (52.5 g, 140.7 mmol) in a mixture of tetrahydrofuran (400 mL), methanol (400 mL) and 1N aqueous sodium hydroxide (280 mL) was heated at ca 50° C. with stirring for 20 minutes. After cooling, the mixture was diluted with water (300 mL) and 1N aqueous HCl (325 mL) was added. After stirring for 45 minutes, the precipitate was filtered, washed well with water and dried to afford the 1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylic acid as a cream-colored solid.

後処理

  1. temperaturewas heated at ca 50° C.
  2. temperatureAfter cooling
  3. additionwas added
  4. stirringAfter stirring for 45 minutes
  5. filtrationthe precipitate was filtered
  6. washwashed well with water
  7. customdried

出典と根拠

ORDレコード
ord-918fa11d986c4d79b36d89a8d037ec14
出典データセット
uspto-grants-2004_06
特許番号
US06743802B2

反応ノート

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