Sodium Hydroxide → HCID 66620914, compound

HRID 415531Notes

Reaction equation

HRID 415531 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][C:16]([Br:21])=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1S(C)(=O)=O)(=O)C.[OH-].[Na+]>O>[Br:21][C:16]1[CH:15]=[C:14]2[C:19]([C:20]3[N:8]4[CH2:7][CH2:6][CH2:5][O:4][C:9]4=[N:10][C:11]=3[CH:12]=[N:13]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 66620157HCID 66620157, compound

Product 1

HCID 66620914HCID 66620914, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round-bottomed flask containing 3-[7-bromo-2-(methylsulfonyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl acetate (15.7 g, 36.8 mmol) was added 2 N NaOH (300 mL) and the reaction was stirred at ambient temperature for 72 h. To the stirred reaction mixture was added additional 2 N NaOH (80 mL) and after 2 h more 2 N NaOH (100 mL) was added. After 1 h the reaction was diluted with water (1.1 L) and transferred to a separatory funnel. The aqueous layer was extracted with dichloromethane (3×800 mL). The aqueous layer was then extracted with ethyl acetate (3×800 mL) and the ethyl acetate extracts were combined, dried (MgSO4), filtered, and the solvent evaporated to afford a solid. The solid was washed with diethyl ether to afford 3-bromo-10,11-dihydro-9H-[1,3]oxazino[3′,2′:1,2]imidazo[4,5-c]quinoline (3.41 g) as a white solid. The dichloromethane extracts were combined and concentrated under reduced pressure. The residue was treated with 2 N NaOH to afford additional product.

Workup

  1. customTo the stirred reaction mixture
  2. customtransferred to a separatory funnel
  3. extractionThe aqueous layer was extracted with dichloromethane (3×800 mL)
  4. extractionThe aqueous layer was then extracted with ethyl acetate (3×800 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customto afford a solid
  9. washThe solid was washed with diethyl ether

Sources & evidence

ORD record
ord-3bc7952a54f7444e966299a4e767453b
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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