Hydrochloric Acid → HCID 86681239, compound

HRID 1848266Notes

Reaction equation

HRID 1848266 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[NH:9]1[CH:13]=[CH:12][CH:11]=[N:10]1.[ClH:14].O1CCOCC1>C(O)C.C(OCC)C>[ClH:14].[N:9]1([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)[CH:13]=[CH:12][CH:11]=[N:10]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1048PyrazoleHCID 312751,4-DioxaneHCID 226075514-Iodopyridin-2-amine

Product 1

HCID 86681239HCID 86681239, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A 20 mL reaction vessel was charged with 4-iodopyridin-2-amine (1.5 g, 6.8 mmol) and 1H-pyrazole (4.0 g, 58.9 mmol). Concentrated hydrochloric acid (1.5 ml) and 1,4-dioxane (1.5 mL) were added, and the reaction vessel was sealed. The mixture was irradiated in a microwave oven at 120° C. for 45 min and then at 130° C. for 60 min. The mixture was cooled to rt and then diethyl ether (6 ml) and ethanol (3 ml) were added. The mixture was sonicated for 10 min, and the solid was collected by filtration and washed with diethyl ether and n-hexane to give 4-(1H-pyrazol-1-yl)pyridin-2-amine hydrochloride (1.2 g, 90%) as a white solid. LCMS (ESI) m/z 161 (M+H)+.

Workup

  1. customA 20 mL reaction vessel
  2. customthe reaction vessel was sealed
  3. customThe mixture was irradiated in a microwave oven at 120° C. for 45 min
  4. customThe mixture was sonicated for 10 min
  5. filtrationthe solid was collected by filtration
  6. washwashed with diethyl ether and n-hexane

Sources & evidence

ORD record
ord-5e73e4fd5ffb47f782b51cb311cd82b4
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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