Ethyl formate → 3-Hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, methyl ester

HRID 1283821ノート

反応式

HRID 1283821 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]([C:15]([O:17][CH3:18])=[O:16])[CH:8]([CH3:19])[CH2:7][C:6]2=[O:20].[CH:21](OCC)=[O:22].[O-]CC.[Na+].[H-].[Na+]>C(O)C.C1C=CC=CC=1>[OH:22][CH:21]=[C:7]1[C:6](=[O:20])[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]([C:15]([O:17][CH3:18])=[O:16])[CH:8]1[CH3:19]

参加物

7

反応物 4

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 2723922Sodium ethoxideHCID 21439723Methyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

生成物 1

HCID 867338533-Hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, methyl ester

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 702Ethanol溶媒

実験手順

Methyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate (13.8 g.) in 140 ml. of benzene containing 19 ml. of ethyl formate is added to sodium ethoxide freshly prepared from 4.8 g. of sodium hydride and 6 ml. of ethanol over a period of 45 min. After stirring at room temperature for 4 hrs. the reaction mixture is poured onto 250 ml. of ice-water. The aqueous layer is retained and the organic layer washed with 1N aqueous sodium hydroxide. The washings are combined with the aqueous extracts and backwashed with benzene. The aqueous layer is then made acid with 12N hydrochloric acid and extracted with chloroform. The organic phase is separated, dried over r magnesium sulfate and evaporated in vacuo to dryness. The residue is employed in subsequent reactions without further purification.

後処理

  1. customfreshly prepared from 4.8 g
  2. additionthe reaction mixture is poured onto 250 ml
  3. washthe organic layer washed with 1N aqueous sodium hydroxide
  4. extractionextracted with chloroform
  5. customThe organic phase is separated
  6. dry with materialdried over r magnesium sulfate
  7. customevaporated in vacuo to dryness
  8. customThe residue is employed in subsequent reactions without further purification

出典と根拠

ORDレコード
ord-da675c4de376466bbdedd22d7f2220a3
出典データセット
uspto-grants-1976_08
特許番号
US03976650

反応ノート

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