Tetrahydrothiopyran-4-one → 10-amino-3,4-dihydro-7-methyl-1H-thiopyrano[4,3-b]quinoline

HRID 1905380

반응식

HRID 1905380 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5](=[CH:8][CH:9]=1)[C:6]#[N:7].[S:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1>[N+](C1C=CC=CC=1)([O-])=O>[NH2:7][C:6]1[C:5]2[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][C:4]=2[N:10]=[C:14]2[CH2:15][CH2:16][S:11][CH2:12][C:13]=12

참가 물질

4

반응물 2

HCID 66173Tetrahydrothiopyran-4-oneHCID 28012762-Amino-4-methylbenzonitrile

생성물 1

HCID 1458024610-amino-3,4-dihydro-7-methyl-1H-thiopyrano[4,3-b]quinoline수율 61.2%

시약·촉매·용매 1

HCID 7416Nitrobenzene용매

반응 조건

온도
50 °C

실험 절차

A mixture of 4-methylanthranilonitrile (4.46 g) and freshly fused zinc (6.8 g) in 20 ml of nitrobenzene was heated at 50° C. for 1 hour. To this was added tetrahydrothiopyran-4-one (5.1 g) and the mixture was heated to 130° C. for 1.5 hours. After cooling, the zinc complex was filtered, rinsed with ethyl ether and partitioned between 2-butanone (MEK) and NH4OH. The aqueous phase was extracted with MEK and the organics were washed with water and dried (saturated NaCl, MgSO4). This was concentrated to give 4.76 g of an off-white powder, m.p. 239°-245° C. d., which was recrystallized from ethyl acetate to give 2.95 g of an off-white powder, m.p. 243°-246° C. d.

후처리

  1. temperaturethe mixture was heated to 130° C. for 1.5 hours
  2. temperatureAfter cooling
  3. filtrationthe zinc complex was filtered
  4. washrinsed with ethyl ether
  5. custompartitioned between 2-butanone (MEK) and NH4OH
  6. extractionThe aqueous phase was extracted with MEK
  7. washthe organics were washed with water
  8. dry with materialdried (saturated NaCl, MgSO4)
  9. concentrationThis was concentrated

출처 및 근거

ORD 기록
ord-66c1691156054a67805ff1c5dc90d727
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04843079

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