Hydrochloric Acid → HCID 53765995, compound

HRID 1584747Notes

Reaction equation

HRID 1584747 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.Cl.[N:12]([O-])=O.[Na+].[C:16]([CH:19](C(=O)C)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(=[O:18])[CH3:17]>N1C=CC=CC=1.C(O)C.O>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][NH:12][CH:19]([C:16](=[O:18])[CH3:17])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:10][CH:9]=2)[CH:5]=[N:6]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 87820Ethyl 3-acetyl-4-oxopentanoateHCID 880121H-Indazol-5-amineHCID 23668193Sodium Nitrite

Product 1

HCID 53765995HCID 53765995, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-aminoindazole in 50 ml. of ethanol, 100 ml. of water and 8 ml. of 12M hydrochloric acid was cooled to 0° C. and a previously cooled solution of 3.41 g. (49.5 mmoles) of sodium nitrite in 10 ml. of water was added dropwise. After 30 minutes, the dark red mixture was added to the solution of 9.2 g, (49.5 mmoles) of ethyl 3-acetyl-4-oxopentanoate in 20 ml. of ethanol and 14.2 ml. of pyridine. The resulting mixture was stirred at 0° C. for 30 minutes and then at room temperature for an additional 30 minutes and finally the solid collected by filtration to give 11.2 g. of solid.

Workup

  1. waitat room temperature for an additional 30 minutes
  2. filtrationfinally the solid collected by filtration
  3. customto give 11.2 g

Sources & evidence

ORD record
ord-9fd921f1baf14516af429ec34b98f8f5
Source dataset
uspto-grants-1999_08
Patent number
US05935957

Reaction notes

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