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

HRID 274230

反応式

HRID 274230 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7416Nitrobenzene溶媒

反応条件

温度
50 °C

実験手順

A mixture of 4-methylanthranilonitrile (4.46 g) and freshly fused zinc chloride (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.

後処理

  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

出典と根拠

ORDレコード
ord-6cbfcb18fdcd4d28be9155cdfde98cdc
出典データセット
uspto-grants-1995_02
特許番号
US05389629

関連ノート

読み込み中…