Water → N-[6-Chlorohexyl]-6-methoxy-4-methyl-8-quinolinamine

HRID 542852Notes

Reaction equation

HRID 542852 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH:13][CH:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH3:21].S(Cl)([Cl:24])=O.O.[OH-].[NH4+]>ClCCl>[Cl:24][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[C:6]2[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 86741428HCID 86741428, compound

Product 1

HCID 608631N-[6-Chlorohexyl]-6-methoxy-4-methyl-8-quinolinamineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 7.8 g (0.027 mole) of 6-[(6-methoxy-4-methyl-8-quinolinyl)amino-1-hexanol in 90 ml of dichloromethane at 5° was added dropwise a solution of 1.9 ml (0.03 mole) of thionylchloride in 25 ml of dichloromethane. The mixture was allowed to warm to room temperature overnight, poured into iced water, and made basic with concentrated ammonium hydroxide. The resulting emulsion was filtered and the layers then separated. The organic portion was washed, dried, and concentrated to afford 7.9 g (96%) of crude product which was used in the next step without further purification. TLC(silica--thyl acetate) indicated that the product, Rf=0.65, was slightly contaminated with the starting hexanol, Rf=0.4.

Workup

  1. filtrationThe resulting emulsion was filtered
  2. customthe layers then separated
  3. washThe organic portion was washed
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e7c025f4b11c41b3b07cdfe3e7f0cba7
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Reaction notes

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