Hydrochloric Acid → HCID 53765995, compound

HRID 399420Notes

Reaction equation

HRID 399420 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

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° 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-beb2a7d2ec5f47c3a9a6e682a9a1170a
Source dataset
uspto-grants-1998_10
Patent number
US05821243

Reaction notes

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