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

HRID 1012704Notes

Reaction equation

HRID 1012704 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

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-e77c683147f1468bab587281d618ecd8
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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