Sodium Hydroxide → 4-Cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid

HRID 572625Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)=[C:5]([C:14]([O:16]CC)=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].[OH-].[Na+]>C1COCC1.O>[C:1]([C:3]1[C:4]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)=[C:5]([C:14]([OH:16])=[O:15])[S:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a slurry of ethyl 4-cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylate (1.04 g, 2.53 mmol) in THF (20 mL) was added 1.0 M of sodium hydroxide in water (20 mL). The reaction mixture was stirred at 80° C. overnight and was concentrated. The residue was diluted with 1 N HCl and a precipitate formed. The precipitate was filtered and dried to give 4-cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid (75) (0.88 g, 91%). LCMS: (FA) ES− 381.2. 1H NMR (400 MHz, d6-DMSO) δ: 13.00 (s, 1H), 7.65-7.72 (m, 2H), 7.36 (d, 1H), 3.73-3.79 (m, 4H) and 3.55-3.61 (m, 4H).

Workup

concentrationwas concentrated
additionThe residue was diluted with 1 N HCl
customa precipitate formed
filtrationThe precipitate was filtered
customdried

Sources & evidence

ORD record: ord-6038eec388644c14ae3fa8a23c99f589
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029411B2

Reaction notes

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