Hydrochloric Acid → Ethyl 2-amino-2-(1-methyl-1H-pyrazol-4-yl)acetate

HRID 923458Notes

Reaction equation

HRID 923458 reaction equation
C1(C(=[N:14][CH:15]([C:21]2[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])C2C=CC=CC=2)C=CC=CC=1.Cl>O1CCOCC1>[NH2:14][CH:15]([C:21]1[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118318070ethyl [(diphenylmethylene)amino](1-methyl-1H-pyrazol-4-yl)acetate

Product 1

HCID 60797101Ethyl 2-amino-2-(1-methyl-1H-pyrazol-4-yl)acetateYield 75.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 228 mg of ethyl [(diphenylmethylene)amino](1-methyl-1H-pyrazol-4-yl)acetate in 2.8 ml of 1,4-dioxane was added 1.9 ml of 1 M hydrochloric acid, followed by stirring at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure, the obtained residue was washed with diethyl ether, and to the aqueous layer was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was then evaporated under reduced pressure to obtain 91 mg of ethyl amino(1-methyl-1H-pyrazol-4-yl)acetate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe obtained residue was washed with diethyl ether
  3. additionto the aqueous layer was added a saturated aqueous sodium hydrogen carbonate solution
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-af32dd5262e1497585e08c1ff4b9245b
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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