3-(Methylsulfonyl)-1-propanol → 4-Chloro-6-cyano-7-(3-methylsulphonylpropoxy)quinoline

HRID 2222417Notes

Reaction equation

HRID 2222417 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:15][S:16]([CH2:19][CH2:20][CH2:21]O)(=[O:18])=[O:17]>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:21][CH2:20][CH2:19][S:16]([CH3:15])(=[O:18])=[O:17])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2004243-(Methylsulfonyl)-1-propanolHCID 1355837304-Chloro-6-cyano-7-hydroxyquinoline

Product 1

HCID 691357954-Chloro-6-cyano-7-(3-methylsulphonylpropoxy)quinolineYield 90.3%

Procedure

Using an analogous procedure to that described for the preparation of the starting material in Example 15, (see note a) above), 4-chloro-6-cyano-7-hydroxyquinoline (300 mg, 1.46 mmol), (prepared as described for the starting material in Example 1), was reacted with 3-(methylsulphonyl)-1-propanol (263 mg, 1.9 mmol) and the crude product was purified using a gradient of methylene chloride/ethyl acetate (1/1) to (2/8) to give 4-chloro-6-cyano-7-(3-methylsulphonylpropoxy)quinoline (428 mg, 90%)

Workup

  1. customthat described for the preparation of the starting material in Example 15
  2. custom(prepared
  3. customthe crude product was purified

Sources & evidence

ORD record
ord-3265bc79fe554a8782e64b3ae2c02397
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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