Hydrochloric Acid → HCID 22180015, compound

HRID 524984Notes

Reaction equation

HRID 524984 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([Cl:7])=[C:3]1[C:8]([O:10]CC1C=CC=CC=1)=[O:9].Cl.C(OCC)C>CO.[Pd]>[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([Cl:7])=[C:3]1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 70922586HCID 70922586, compound

Product 1

HCID 22180015HCID 22180015, compoundYield 103.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 1-amino-3-chloro-1H-pyrrole-2-carboxylate (20.56 g, 0.08 mol) in methanol (205 mL) was added 32.1 mL of a 3M methanolic solution of HCl (0.1 mol) and 7.7 g (0.07 mol) of 10% palladium on charcoal and this mixture was submitted to hydrogenation in a Parr apparatus working at 25 psi and room temperature during 21 hours. At the end of this period, the reaction was stopped filtering palladium catalyst through a pad of Celite® and the filtrate was concentrated in vacuum to give a light brown solid that was macerated with 40 mL of diethyl ether. This solid was filtrated and washed with petroleum ether to yield 13.32 g of the title compound with a purity of 55% (59% yield) being the dehalogenated compound the main impurity. No further purifications were done proceeding to the next step.

Workup

  1. filtrationAt the end of this period, the reaction was stopped filtering palladium catalyst through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuum
  3. customto give a light brown solid that
  4. filtrationThis solid was filtrated
  5. washwashed with petroleum ether

Sources & evidence

ORD record
ord-636bc287946a4d028ee5169912f8813e
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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