Lithium hydroxide, monohydrate → 6-Cyano-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

HRID 518129Notes

Reaction equation

[C:1]([C:3]1[C:4]2[S:15][C:14]([CH3:16])=[CH:13][C:5]=2[NH:6][C:7]=1[C:8]([O:10]CC)=[O:9])#[N:2].O.[OH-].[Li+]>O1CCCC1.C(O)C.O>[C:1]([C:3]1[C:4]2[S:15][C:14]([CH3:16])=[CH:13][C:5]=2[NH:6][C:7]=1[C:8]([OH:10])=[O:9])#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixed solution of ethyl 6-cyano-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate (0.64 g) in tetrahydrofuran (8.0 mL), ethanol (4.0 mL) and water (6.0 mL) was added lithium hydroxide monohydrate (1.14 g), and the mixture was stirred at 50° C. for 35 hours. The reaction solution was concentrated under reduced pressure. To the residue was added 2 mol/L hydrochloric acid (18 mL) and water. The precipitated solid was collected by filtration, washed with water, and dried under reduced pressure at 50° C. to give the title compound (0.59 g).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
additionTo the residue was added 2 mol/L hydrochloric acid (18 mL) and water
filtrationThe precipitated solid was collected by filtration
washwashed with water
customdried under reduced pressure at 50° C.

Sources & evidence

ORD record: ord-88f4a6568e654ec1be3c96100635b507
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115144B2

Reaction notes

Loading…