4-Toluenesulfonyl chloride → 5,6,7,8-Tetrahydro-3-methyl-8-(4-methylbenzenesulphonylamino) quinoline hydrochloride

HRID 359456Notes

Reaction equation

HRID 359456 reaction equation
[NH2:1][CH:2]1[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([Cl:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[ClH:23].[CH3:12][C:8]1[CH:9]=[N:10][C:11]2[CH:2]([NH:1][S:20]([C:17]3[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=3)(=[O:22])=[O:21])[CH2:3][CH2:4][CH2:5][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 123582203-Methyl-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 146209655,6,7,8-Tetrahydro-3-methyl-8-(4-methylbenzenesulphonylamino) quinoline hydrochlorideYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

8-Amino-5,6,7,8-tetrahydro-3-methyl-quinoline (3.07g) was dissolved in CH2Cl2 [(250ml) and 4-methylbenzenesulphonyl-chloride (2.68g) was added in CH2Cl2 (25ml) followed by triethylamine (25ml) in CH2Cl2 (25ml). The reaction mixture was stirred at room temperature until t.l.c. showed all the starting material to have reacted. The solvent was removed under reduced pressure and the residue was dissolved in 2N.HCl (200ml) and extracted with Et2O (2×100ml). The acid solution was then basified with solid K2CO3 and was extracted with CH2Cl2 (3×100ml). The extracts were dried (MgSO4) and evaporated to low volume under reduced pressure. The residue was treated with Et2O/HCl to give a white solid which was recrystallised from EtOH to give 5,6,7,8-tetrahydro-3-methyl-8-(4-methylbenzenesulphonylamino) quinoline hydrochloride (2.1g). mp. 214° C. decomp. (Found: C,58.3; H,6.2; N,7.7. C17H21N 2 SO2Cl requires: C,58.0; H,6.0; N,7.8%).

Workup

  1. customto have reacted
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in 2N
  4. extractionHCl (200ml) and extracted with Et2O (2×100ml)
  5. extractionwas extracted with CH2Cl2 (3×100ml)
  6. dry with materialThe extracts were dried (MgSO4)
  7. customevaporated to low volume under reduced pressure
  8. additionThe residue was treated with Et2O/HCl
  9. customto give a white solid which
  10. customwas recrystallised from EtOH

Sources & evidence

ORD record
ord-67a3dc4f9c524b41abe4fdc6d09f6a3a
Source dataset
uspto-grants-1991_03
Patent number
US05001131

Reaction notes

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