Hydrochloric Acid → HCID 53765995, compound

HRID 567700Notes

Reaction equation

HRID 567700 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 12 M 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-63205fa27670449ba93c78732506cce7
Source dataset
uspto-grants-2001_01
Patent number
US06180628B2

Reaction notes

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