Hydrochloric Acid → 6-Cyclopropylpyridin-2-amine

HRID 531443Notes

Reaction equation

HRID 531443 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([NH:10]C(=O)C(C)(C)C)[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.Cl>O1CCOCC1.C(OCC)(=O)C>[CH:1]1([C:4]2[N:9]=[C:8]([NH2:10])[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 60019882N-(6-Cyclopropyl-pyridin-2-yl)-2,2-dimethyl-propionamide

Product 1

HCID 457878636-Cyclopropylpyridin-2-amineYield 77.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-(6-cyclopropylpyridin-2-yl)pivalamide (4.25 gm, 19.49 mmol) in dioxane (34 ml) was added 9N HCl (34 ml). The mixture was stirred for 18 hours at 90° C. After cooling to 25° C., the pH of the reaction was adjusted with to achieve pH-9. The solution was diluted with ethyl acetate (200 ml) quantity and washed with saturated sodium bicarbonate. Next, the organic portion was dried over sodium sulfate and concentrated to get 2 gm (77.5% yield) clear oil.

Workup

  1. temperatureAfter cooling to 25° C.
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialNext, the organic portion was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a034a10a9ee499ab6e3d2523d91d625
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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