Hydrochloric Acid → HCID 19086734, compound

HRID 1464567Notes

Reaction equation

HRID 1464567 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][CH:5]=1)([O-])=O.O.Cl>C(O)(C)C>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19086744HCID 19086744, compound

Product 1

HCID 19086734HCID 19086734, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Ethyl 2-(6-nitroindazol-1-yl)propionate (1 g), water (3.7cm3) and reduced iron (2.3 g) were stirred in isopropanol (17cm3) at room temperature. Concentrated hydrochloric acid (0.14cm3) was added and the mixture stirred and heated under reflux for 20 minutes. The mixture was filtered through hyflo whilst hot and filter pad washed with ethanol. The combined filtrate was concentrated under vacuum and the residue purified by chromatography (SiO2 ; CHCl3 : ether, 3:1) to give ethyl 2-(6 aminoindazol-1-yl)propionate (0.649). M+ =233

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 minutes
  3. filtrationThe mixture was filtered through hyflo whilst hot and
  4. filtrationfilter pad
  5. washwashed with ethanol
  6. concentrationThe combined filtrate was concentrated under vacuum
  7. customthe residue purified by chromatography (SiO2 ; CHCl3 : ether, 3:1)

Sources & evidence

ORD record
ord-bc58dc7dec7a486788fd02df819c2d14
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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