Hydrochloric Acid → HCID 178475363, compound

HRID 1749927Notes

Reaction equation

HRID 1749927 reaction equation
C([O:4][C:5]1C=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10]C=[CH:8]2)(=O)C.[OH2:14].[N:15]([O-])=O.[Na+].Cl.O1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[C:24]([O:23][C:22]1[CH:21]=[C:12]2[C:11](=[CH:7][CH:8]=1)[NH:10][N:15]=[C:13]2[CH:5]=[O:4])(=[O:14])[CH3:25]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 116007575-AcetoxyindoleHCID 23668193Sodium Nitrite

Product 1

HCID 178475363HCID 178475363, compoundYield 49%

Procedure

A solution of 1H-indol-5-yl acetate (0.175 g, 1.00 mmol) in 1,4-dioxane (10 mL) was added with water (120 mL), and the mixture was stirred at room temperature. The reaction mixture was added with sodium nitrite (0.690 g, 10.0 mmol), and the mixture was cooled to 0° C. The reaction mixture was added dropwise with 3 N hydrochloric acid (2.00 mL, 6.00 mmol) at 0° C., and then the mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered, and then the filtrate was extracted three times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated to obtain 3-formyl-1H-indazol-5-yl acetate (0.100 g, 49%).

Workup

  1. temperaturethe mixture was cooled to 0° C
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. filtrationThe reaction mixture was filtered
  4. extractionthe filtrate was extracted three times with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fbda715cb1764b4c9a33e338255b7be4
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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