Acetic Acid → Ethyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate

HRID 1176233노트

반응식

HRID 1176233 반응식
C([C:3]1[C:11]([N+:12]([O-])=O)=[C:10]([CH:15]=[CH:16][C:17]([O:19]C)=O)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])C.[C:21](O)(=O)[CH3:22]>[Pd]>[O:19]=[C:17]1[CH2:16][CH2:15][C:10]2[C:11](=[CH:3][C:4]([C:5]([O:7][CH2:21][CH3:22])=[O:6])=[CH:8][CH:9]=2)[NH:12]1

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 68501280Ethyl 4-(2-methoxycarbonylvinyl)-3-nitrobenzoic acid

생성물 1

HCID 23112273Ethyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate

시약·촉매·용매 1

HCID 23938Palladium촉매

반응 조건

온도
70 °C

실험 절차

The solution of 2.80 g of ethyl 4-(2-methoxycarbonylvinyl)-3-nitrobenzoic acid in 20 ml of glacial acetic acid is hydrogenated in the presence of 0.288 g of 10% Pd/C at room temperature over 16 hours. The reaction mixture is stirred at 70° C. over 1 hour and subsequently concentrated by evaporation to dryness. The residue is admixed with 250 ml of 1M sodium hydrogencarbonate and extracted with ethyl acetate (2×250 ml). The organic phases are washed with water (250 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a white solid from the residue by means of crystallization (ethyl acetate-hexane). Rf=0.24 (1:1 EtOAc-heptane).

후처리

  1. concentrationsubsequently concentrated by evaporation to dryness
  2. extractionextracted with ethyl acetate (2×250 ml)
  3. washThe organic phases are washed with water (250 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-965d6892477a4f15938e0d95d999d77b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842688B2

반응 노트

불러오는 중…