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

HRID 2074008노트

반응식

HRID 2074008 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

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온도
25 °C

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-9d754c7a06e14d3ba3914a8e7d266380
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04920219

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