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

HRID 328813노트

반응식

HRID 328813 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 702Ethanol용매

실험 절차

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 hdyroxide. The washings are combined with the aqueous extracts and backwashed with benzene. The aqueous layer is then made acid with 12N hdyrochloric acid and extracted with chloroform. The organic phase is separated, dried over magnesium sulfate and evaporated in vacuo to dryness. The residue is employed in subsequent reactions without further purification.

후처리

  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 hdyroxide
  4. extractionextracted with chloroform
  5. customThe organic phase is separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo to dryness
  8. customThe residue is employed in subsequent reactions without further purification

출처 및 근거

ORD 기록
ord-a497f81fb3194ca0a90c55877d29ed5d
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04018758

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