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

HRID 2179578
Notes
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Reaction equation

HRID 2179578 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58485644Methyl 7-[4-(4-morpholinyl)phenyl]-1-benzothiophene-2-carboxylate

Product 1

HCID 179826497-[4-(4-Morpholinyl)phenyl]-1-benzothiophene-2-carboxylic acidYield 111.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionafter addition of water
  3. filtrationThe resulting precipitate is filtered off with suction
  4. washwashed twice with water
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes