Potassium Hydroxide → 7-[4-(4-Morpholinyl)phenyl]-1-benzothiophene-2-carboxylic acid

HRID 2179578Notes

Reaction equation

[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:21]4[S:20][C:19]([C:22]([O:24]C)=[O:23])=[CH:18][C:17]=4[CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[K+]>CO>[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:21]4[S:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][C:17]=4[CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 330 mg (0.77 mmol) of methyl 7-[4-(4-morpholinyl)phenyl]-1-benzothiophene-2-carboxylate (Example 19A) in 6 ml of a 1:1 mixture of methanol and 2N potassium hydroxide solution is stirred at room temperature for 2 h and at 50° C. for 1 h. The reaction mixture is concentrated in vacuo and, after addition of water, acidified with conc. hydrochloric acid. The resulting precipitate is filtered off with suction, washed twice with water and dried under high vacuum. 292 mg of crude product are obtained and reacted without further purification.

Workup

concentrationThe reaction mixture is concentrated in vacuo
additionafter addition of water
filtrationThe resulting precipitate is filtered off with suction
washwashed twice with water
customdried under high vacuum

Sources & evidence

ORD record: ord-cea1042eacfe4ac5a52aa44cd093ba0d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067931B2

Reaction notes

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