Water → 4-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-(3-chloropropoxy)quinoline

HRID 1830790Notes

Reaction equation

HRID 1830790 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[O:5][C:6]1[CH:27]=[CH:26][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:23])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:24]#[N:25])=[CH:8][CH:7]=1.[Cl:32][CH2:33][CH2:34][CH2:35]Br.[O-]CCCC.[K+].O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[O:5][C:6]1[CH:27]=[CH:26][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH2:35][CH2:34][CH2:33][Cl:32])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:24]#[N:25])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 23699084Potassium butoxideHCID 1358198314-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-hydroxyquinoline

Product 1

HCID 220485174-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-(3-chloropropoxy)quinolineYield 77.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The product of step 2 (206.5 mg, 0.5 mmole) and 1-chloro-3-bromopropane (95 mg, 0.6 mmole) was dissolved in dimethylsulphoxide (5 ml) in the presence of potassium butoxide (0.55 ml, 1.0M in THF, 0.55 mmole) in and the mixture held at room temperature for 18 hours. Water was added and the mixture extracted with ethyl acetate. The combined extracts were washed with water and brine then dried (MgSO4) and evaporated to give 4-(4-(2-methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-(3-chloropropoxy)quinoline (189 mg, 77%) as a yellow gum.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialthen dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-4b9c4aceac754c30be0134e24e420080
Source dataset
uspto-grants-2006_06
Patent number
US07067532B2

Reaction notes

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