Morpholine → 1H-Indazole, 3-(4-morpholinyl)-5-nitro-

HRID 1037993Notes

Reaction equation

HRID 1037993 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][N:3]=1.C(OC(=O)C)C.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[N:20]1([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=3)[NH:4][N:3]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 178526490HCID 178526490, compound

Product 1

HCID 30513261H-Indazole, 3-(4-morpholinyl)-5-nitro-

Procedure

3-Bromo-5-nitro-1H-indazole (0.5 gm, 2 mmol) was dissolved in 3.5 ml of morpholine and heated in a sealed tube for 40 hrs. The mixture was then cooled and added to ethylacetate, washed with brine and dried over magnesium sulfate. After chromatography on silica gel using 20-50% ethylacetate/hexanes as eluent the title compound was obtained (210 mg, 0.85 mmol).

Workup

  1. temperatureheated in a sealed tube for 40 hrs
  2. temperatureThe mixture was then cooled
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-377ab11a9bd34dd09826aca08ae5447a
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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