Sodium Carbonate → HCID 10359250, compound

HRID 1672342Notes

Reaction equation

HRID 1672342 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[CH:13][N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1.C(=O)([O-])[O-:23].[Na+].[Na+].ClC1C=C(C=CC=1)C(OO)=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N+:8]([O-:23])=[CH:7][C:6]3[N:12]=[CH:13][N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium Carbonate2×HCID 70297m-Chloroperbenzoic acid2×HCID 10448328HCID 10448328, compound

Product 1

HCID 10359250HCID 10359250, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3.01 g (9.508 mmol) 8-chloro-1-(2-chloro-phenyl)-1H-imidazo[4,5-c]quinoline (Example 25), 1.22 g (11.4 mmol) sodium carbonate and 2.6 g (10.45 mmol) 3-chloroperoxybenzoic acid in 75 ml chloroform are stirred at rt for 5 h. After this time, a further amount of 254 mg of sodium carbonate, 472 mg 3-chloroperoxybenzoic acid and 50 ml chloroform are added and stirring is continued for 2 h at 50° C. The cold solution is washed with sat. sodium bicarbonate solution (2×), 0.1 N sodium thiosulfate (2×) and brine (2×). The organic phase is dried over sodium sulfate and the solvent evaporated. Purification of the title compound is achieved by chromatography (CH2Cl2-methanol 95:5→90:10) and crystallization (ethyl acetate-hexane). mp: 247-250° C.; MS: 330 (M++1); HPLC: tret=11.25 min (Grad 1).

Workup

  1. washThe cold solution is washed with sat. sodium bicarbonate solution (2×), 0.1 N sodium thiosulfate (2×) and brine (2×)
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customthe solvent evaporated
  4. customPurification of the title compound
  5. customis achieved by chromatography (CH2Cl2-methanol 95:5→90:10) and crystallization (ethyl acetate-hexane)
  6. customtret=11.25 min (Grad 1)

Sources & evidence

ORD record
ord-8f4972ae038c4a9b9b4ac0ac673d4316
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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