Hydrochloric Acid → HCID 12140098, compound

HRID 1473179Notes

Reaction equation

[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]1[C:15]([O:17]CC)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].Cl>CO.O1CCCC1>[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]1[C:15]([OH:17])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of ethyl 1-benzyl-3-cyano-1H-pyrrole-2-carboxylate (8.7 g, 34.1 mmol) in Methanol (40 mL) and Tetrahydrofuran (THF) (40 mL) was treated with 2M LiOH (40 mL, 80 mmol) and then stirred at 50° C. for 1 hour. The mixture was adjusted to pH<2 by adding HCl (1M) and then concentrated to afford 1-benzyl-3-cyano-1H-pyrrole-2-carboxylic acid as a white solid (7.3 g, 32.4 mmol, 95% yield) which was used in the next step without any further purification. 1H NMR (400 MHz, DMSO-d6) ppm 7.54 (d, J=6.4 Hz, 1H), 7.45-7.27 (m, 4H), 7.12 (d, J=7.2 Hz, 1H), 6.76-6.69 (d, J=7.2 Hz, 1H), 5.64 (s, 2H); LCMS (m/z) ES+=227 (M+1).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-bb4afeab5af84a718c8fb0fb09dcd7b0
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012642B2

Reaction notes

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