Dichloromethane methanol → 4-Cyclopropylpyridin-3-amine

HRID 705360Notes

Reaction equation

HRID 705360 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[NH:10]C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.CO.C(Cl)Cl>Cl.O1CCOCC1>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[NH2:10])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 67981637Tert-butyl 4-cyclopropylpyridin-3-ylcarbamate

Product 1

HCID 668019694-Cyclopropylpyridin-3-amineYield 144.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 4-cyclopropylpyridin-3-ylcarbamate (393 mg, 1.677 mmol) was dissolved in 4 M HCl in dioxane (30 mL), and stirred at room temperature for 1 hour, the reaction rapidly becoming a white heterogeneous mixture. TLC (SiO2, 5% methanol/CH2Cl2) showed reaction complete after 1 hour. The solvent was removed by rotary evaporation, the residue was triturated with diethyl ether and vacuum filtered to collect the solid, and the solid was dried in a vacuum oven at 50° C. for 1 hour to afford the product as a beige solid (325 mg).

Workup

  1. customthe reaction
  2. customreaction complete after 1 hour
  3. customThe solvent was removed by rotary evaporation
  4. customthe residue was triturated with diethyl ether and vacuum
  5. filtrationfiltered
  6. customto collect the solid
  7. customthe solid was dried in a vacuum oven at 50° C. for 1 hour

Sources & evidence

ORD record
ord-35f586d1acbf46cd81d8712eaa622790
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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