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

HRID 274232ノート

反応式

HRID 274232 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([NH2:11])[C:6](=[CH:9][CH:10]=1)[C:7]#[N:8].[S:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>[N+](C1C=CC=CC=1)([O-])=O.[Cl-].[Zn+2].[Cl-]>[NH2:8][C:7]1[C:6]2[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:13])[F:1])=[CH:4][C:5]=2[N:11]=[C:17]2[CH2:18][CH2:19][S:14][CH2:15][C:16]=12

参加物

5

反応物 2

HCID 66173Tetrahydrothiopyran-4-oneHCID 134390282-Amino-4-(trifluoromethyl)benzonitrile

生成物 1

HCID 1458024810-amino-3,4-dihydro-7-trifluoromethyl-1H-thiopyrano[4,3-b]quinoline収率 54.7%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 7416Nitrobenzene溶媒

反応条件

温度
50 °C

実験手順

To a solution of 4-trifluoromethyl anthranilonitrile (12.2 g) in 50 ml of nitrobenzene was added freshly fused and pulverized zinc chloride (13.4 g). This was stirred at 50° C. for 1.5 hours after which was added tetrahydrothiopyran-4-one (9.9 g). The reaction mixture was stirred at 130° C. for 2 hours and allowed to cool, and the resulting complex was filtered and rinsed with ethyl ether. The solid was partitioned between 2-butanone (MEK) and NH4OH and the aqueous phase was extracted with MEK (2x). The organics were washed with water, dried (saturated NaCl, MgSO4) and concentrated to give 10.2 g of a yellow powder m.p. 253°-259° C. d. A 3.7 g portion was recrystallized from methanol/water to give 3.0 g of an off-white powder, m.p. 258°-262° C. d.

後処理

  1. stirringThe reaction mixture was stirred at 130° C. for 2 hours
  2. temperatureto cool
  3. filtrationthe resulting complex was filtered
  4. washrinsed with ethyl ether
  5. customThe solid was partitioned between 2-butanone (MEK) and NH4OH
  6. extractionthe aqueous phase was extracted with MEK (2x)
  7. washThe organics were washed with water
  8. dry with materialdried (saturated NaCl, MgSO4)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-42af26254de34ba5ac0ffc2ed849e28d
出典データセット
uspto-grants-1995_02
特許番号
US05389629

反応ノート

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