Sodium Hydroxide → ethyl 4-chloro-5-methyl-1H-pyrrole-2-carboxylate

HRID 2233811Notes

Reaction equation

HRID 2233811 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[NH:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][CH:11]=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:11]1[CH:12]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:14][C:10]=1[CH3:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 965981H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl ester2×

Product 1

HCID 66707189ethyl 4-chloro-5-methyl-1H-pyrrole-2-carboxylateYield 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

N-Chlorosuccinimide (0.67 g, 5.08 mmol) was added to a solution of ethyl 5-methyl-1H-pyrrole-2-carboxylate (Intermediate 20) (0.65 g, 4.23 mmol) in chloroform (20 ml). The reaction was warmed to 40° C. and stirred for 4 hours, then poured to a beaker containing 2 N NaOH (20 ml) at 0° C. The layers were separated and the aqueous layer was extracted with chloroform (×3). The combined organic extracts were dried over magnesium sulfate and concentrated. The resultant off-white solid was purified by flash chromatography (hexanes/EtOAc, 16:1) to give the title product as a white solid (0.3 g, 38%).

Workup

  1. additionpoured to a beaker
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with chloroform (×3)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant off-white solid was purified by flash chromatography (hexanes/EtOAc, 16:1)

Sources & evidence

ORD record
ord-1fb3685a69b247dabb0bc5b30cd2f009
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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