Sodium Hydroxide → 1-[(pyridin-2-yl)methyl]-1H-pyrazol-3-amine

HRID 883044Notes

Reaction equation

HRID 883044 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[OH-].[Na+].[H-].[Na+].[NH:14]1[CH:18]=[CH:17][C:16]([N:19]2C(=O)C3C(=CC=CC=3)C2=O)=[N:15]1>O.CN(C=O)C>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][N:14]1[CH:18]=[CH:17][C:16]([NH2:19])=[N:15]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 24758Sodium hydrideHCID 178514958HCID 178514958, compound

Product 1

HCID 470027701-[(pyridin-2-yl)methyl]-1H-pyrazol-3-amineYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1.3 2-Chloromethylpyridine hydrochloride (1.0.9 mmol) is dissolved in water and NaOH (32% in water) is added and extracted with dichloromethane. The combined organic layers are dried over MgSO4 and the solvent is removed in vacuo. The remaining residue is added to a suspension of NaH (2 eq.) in DMF at 0° C. Afterwards 2-(1H-Pyrazole-3-yl)-isoindole-1,3-dione (11.7 mmol) is added and the reaction is stirred 15 hours at 50° C. The solvent is removed in vacuo. Hydrazine hydroxide (20 ml) and ethanol (20 ml) is added and the reaction is stirred 3 days at 120° C. The solvent is removed in vacuo and the residue is suspended in dichloromethane and filtrated. The solvent of the filtrate is removed in vacuo. The remaining residue is purified via column chromatography (ethyl acetate/methanol). 1-Pyridine-2-ylmethyl-1H-pyrazole-3-ylamine is isolated as a yellow powder in a yield of 20%; HPLC (Method B): 0.49 min; LC-MS: 0.550 min, 175.15 (M+H+);

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. customthe solvent is removed in vacuo
  4. customThe solvent is removed in vacuo
  5. additionHydrazine hydroxide (20 ml) and ethanol (20 ml) is added
  6. stirringthe reaction is stirred 3 days at 120° C
  7. customThe solvent is removed in vacuo
  8. filtrationfiltrated
  9. customThe solvent of the filtrate is removed in vacuo
  10. customThe remaining residue is purified via column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-8daf59eb299f4cb4b88f89a2d1cc63e7
Source dataset
uspto-grants-2012_08
Patent number
US08236824B2

Reaction notes

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