Sulfuric Acid → HCID 135800032, compound

HRID 1464568Notes

Reaction equation

HRID 1464568 reaction equation
N[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:19].N([O-])=O.[Na+].NC(N)=O>O.[Cu-]=O>[OH:19][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 1176UreaHCID 19086734HCID 19086734, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135800032HCID 135800032, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(6-aminoindazol-1-yl)propionate (0.49 g) was stirred with hot 35% sulphuric acid (2.12cm3), ice (2.12 g) added and the mixture cooled in an ice/salt bath. Sodium nitrite (0.187 g) in water (2cm3) was added dropwise at 0° C. The mixture was stirred for 5 minutes at 0° C. and a few crystals of urea added. Hydrated copper (II) nitrate (8 g) in water (74cm3) was then added followed by copper (I) oxide (0.3 g) and the mixture stirred for 15 minutes at 0° C. and 1.5 hours at hours at room temperature. The reaction mixture was extracted with ethyl acetate four times, the combined organic extracts washed with water, dried (MgSO4), filtered and the filtrate concentrated under vacuum. The residue was purified by chromatography (SiO2, diethyl ether; then hexane: diethyl ether, 35:65) to give ethyl 2-(6-hydroxyindazol-1-yl)propionate (30 mgs)

Workup

  1. additionadded
  2. temperaturethe mixture cooled in an ice/salt bath
  3. stirringthe mixture stirred for 15 minutes at 0° C. and 1.5 hours at hours at room temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate four times
  5. washthe combined organic extracts washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under vacuum
  9. customThe residue was purified by chromatography (SiO2, diethyl ether

Sources & evidence

ORD record
ord-50abc2764dd6461d8936da9dcd69b664
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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