m-Chloroperbenzoic acid → 3-(2-Butyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)propyl pentanoate

HRID 2090239Notes

Reaction equation

HRID 2090239 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([O:18][CH2:19][CH2:20][CH2:21][N:22]1[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:24]=[C:23]1[CH2:35][CH2:36][CH2:37][CH3:38])(=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]>C(Cl)Cl>[C:12]([O:18][CH2:19][CH2:20][CH2:21][N:22]1[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N+:27]([O-:6])=[CH:26][C:25]=2[N:24]=[C:23]1[CH2:35][CH2:36][CH2:37][CH3:38])(=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 684315713-(2-Butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl pentanoate

Product 1

HCID 684324413-(2-Butyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)propyl pentanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (1.6 g) was added to a solution of the product from step (iii) (2.15 g) in DCM (30 mL) at 5° C. The reaction mixture was allowed to warm to rt, stirred for 18 h and partitioned between DCM/saturated sodium bisulfate solution. The organics were separated washed with saturated NaHCO3 solution, water, dried and evaporated under reduced pressure. Yield 1.77 g

Workup

  1. custompartitioned between DCM/saturated sodium bisulfate solution
  2. customThe organics were separated
  3. washwashed with saturated NaHCO3 solution, water
  4. customdried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-09a1a794701c4dbb91487aed8b6c11a4
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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