Sodium Bicarbonate → HCID 22732733, compound

HRID 2084289Notes

Reaction equation

HRID 2084289 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:18]3[CH2:17][C:16]([CH3:20])([CH3:19])[CH2:15][C:14](=[O:21])[C:13]=3[C:12]([CH3:22])=[N:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:18]3[CH2:17][C:16]([CH3:19])([CH3:20])[CH2:15][C:14](=[O:21])[C:13]=3[C:12]([CH3:22])=[N:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22732706HCID 22732706, compound

Product 1

HCID 22732733HCID 22732733, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Stannous chloride dihydrate (0.94 g, 4.2 mmol) was added to a solution of 1-(3-nitrophenyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole (0.25 g, 0.84 mmol), prepared as described in example 3, in ethanol (5 ml). The reaction mixture was heated at 70° C. for about 1 hour, cooled to room temperature, poured onto ice, neutralized with 5% sodium bicarbonate and extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel (cyclohexane:ethyl acetate=60:40) to give the title compound as a colourless solid (0.125 g, 60%): m.p. 131-132° C.

Workup

  1. customprepared
  2. temperaturecooled to room temperature
  3. additionpoured onto ice
  4. extractionextracted with dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel (cyclohexane:ethyl acetate=60:40)

Sources & evidence

ORD record
ord-f255c41ddeb54138ab8953c923f5525a
Source dataset
uspto-grants-2004_04
Patent number
US06716856B1

Reaction notes

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