4-Toluenesulfonyl chloride → 6-Carbomethoxy-8-chloro-5-methoxy-1,2,3,4-tetrahydroquinoline

HRID 2074008ノート

反応式

HRID 2074008 の反応式
O[CH2:2][CH2:3][CH2:4][C:5]1[C:6]([O:17][CH3:18])=[C:7]([CH:12]=[C:13]([Cl:16])[C:14]=1[NH2:15])[C:8]([O:10][CH3:11])=[O:9].C(N(CC)CC)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[C:8]([C:7]1[C:6]([O:17][CH3:18])=[C:5]2[C:14](=[C:13]([Cl:16])[CH:12]=1)[NH:15][CH2:2][CH2:3][CH2:4]2)([O:10][CH3:11])=[O:9]

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 14883230Methyl 3-(3-hydroxypropyl)-2-methoxy-4-amino-5-chlorobenzoate

生成物 1

HCID 148832316-Carbomethoxy-8-chloro-5-methoxy-1,2,3,4-tetrahydroquinoline

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

A mixture of the compound of step 4 above (1.4 g), triethylamine (1 ml) and TsCl (1.1 g) in CH2Cl2 is stirred at 25° C. for three days. The mixture is washed with saturated aqueous NaHCO3 and evaporated affording a residue which is dissolved in toluene and refluxed for 21/2 hours. The toluene is evaporated and the residue is dissolved in CH2Cl2 and washed with saturated NaHCO3 (25 mls). The organic layer is dried, evaporated and the residue chromatographed on silica gel affording a gum which crystallizes from HexEt2O to give the desired product (M.P. 105°-108° C.).

後処理

  1. washThe mixture is washed with saturated aqueous NaHCO3
  2. customevaporated
  3. customaffording a residue which
  4. temperaturerefluxed for 21/2 hours
  5. customThe toluene is evaporated
  6. dissolutionthe residue is dissolved in CH2Cl2
  7. washwashed with saturated NaHCO3 (25 mls)
  8. customThe organic layer is dried
  9. customevaporated
  10. customthe residue chromatographed on silica gel affording a gum which
  11. customcrystallizes from HexEt2O

出典と根拠

ORDレコード
ord-9d754c7a06e14d3ba3914a8e7d266380
出典データセット
uspto-grants-1990_04
特許番号
US04920219

反応ノート

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