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

HRID 1948296Notes

Reaction equation

ClN1C(=O)C[CH2:4][C:3]1=O.Cl[C:10]1[C:14]([Cl:15])=[C:13]([CH3:16])[NH:12][C:11]=1[C:17]([OH:19])=[O:18].[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:15][C:14]1[CH:10]=[C:11]([C:17]([O:19][CH2:3][CH3:4])=[O:18])[NH:12][C:13]=1[CH3:16]

Participants

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 3; 0.65 g, 4.23 mmol) in chloroform (20 ml). The reaction was warmed to 40° C. and stirred for 4 h, 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%). MS (ES): 188 (M+1) for C8H10ClNO2; NMR (CDCl3): 1.34 (t, 3H), 2.27 (s, 3H), 4.30 (q, 2H), 6.76 (s, 1H), 9.07 (brs, 1H).

Workup

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

Sources & evidence

ORD record: ord-239c79f6d7d74639a67b0d4942d5c76d
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399489B2

Reaction notes

Loading…