Sodium Carbonate → HCID 67051118, compound

HRID 598351Notes

Reaction equation

HRID 598351 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([O:19][C:20]1[CH:29]=[CH:28][C:27]2[N:26]=[CH:25][C:24]3[N:30]=[C:31]([CH2:37][O:38][CH3:39])[N:32]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:23]=3[C:22]=2[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:12]([O:19][C:20]1[CH:29]=[CH:28][C:27]2[N+:26]([O-:6])=[CH:25][C:24]3[N:30]=[C:31]([CH2:37][O:38][CH3:39])[N:32]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:23]=3[C:22]=2[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 67051018HCID 67051018, compound

Product 1

HCID 67051118HCID 67051118, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (60% pure, 3.5 g, 12.3 mmol) was added portionwise to a solution of 8-benzyloxy-1-(2-methylpropyl)-2-methoxymethyl-1H-imidazo[4,5-c]quinoline (4.2 g, 11.19 mmol) in 200 mL of dichloromethane. The reaction was stirred at ambient temperature for 2 hours, and then 100 mL of 2% aqueous sodium carbonate was added. The aqueous layer was extracted with two 100 mL portions of dichloromethane and the organic fractions were combined, dried, and concentrated to give 4.3 g of crude 8-benzyloxy-1-(2-methylpropyl)-2-methoxymethyl-5-oxido-1H-imidazo[4,5-c]quinoline as a light brown solid.

Workup

  1. extractionThe aqueous layer was extracted with two 100 mL portions of dichloromethane
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-775c594e31c4498bb9d60fdaf1d1b6c2
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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