Nitric Acid → HCID 22625623, compound

HRID 277666Notes

Reaction equation

HRID 277666 reaction equation
[Cl:1][C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18].[N+:19]([O-])([OH:21])=[O:20]>>[Cl:1][C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:5]2=[N:4][C:3]=1[C:11]1[CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 22625603HCID 22625603, compound

Product 1

HCID 22625623HCID 22625623, compound

Conditions

Temperature
0 °C

Procedure

A 1.1 g (3.85 mmol) sample of 3-chloro-2-(2,4-dichlorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine was added to 8.0 ml of a 1:1 mixture of concentrated sulfuric/nitric acid at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes followed by warming to 20° C. After pouring the reaction mixture onto ice/water, the resulting aqueous mixture was extracted with 400 ml of ethyl acetate. The separated organic layer was washed with water, brine, and dried over magnesium sulfate. The yellow oily solid residue obtained after evaporating in vacuo was flash chromatographed on silica gel (1:1 hexane/ethyl acetate) to provide 0.8 g of the title compound as a yellow solid (m.p. 111-112° C.). NMR (CDCl3, 200 MHz): δ1.95 (m, 2H), 2.05 (m, 2H), 2.91 (t, 2H), 3.92 (t, 2H), 7.66 (s, 1H), 8.09 (s, 1H).

Workup

  1. temperatureby warming to 20° C
  2. additionAfter pouring the reaction mixture onto ice/water
  3. extractionthe resulting aqueous mixture was extracted with 400 ml of ethyl acetate
  4. washThe separated organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customThe yellow oily solid residue obtained
  7. customafter evaporating in vacuo
  8. customchromatographed on silica gel (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0cdc98424b7246dca060253e57ecec15
Source dataset
uspto-grants-2002_03
Patent number
US06358885B1

Reaction notes

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