Potassium Hydroxide → 6-[(2-Benzylsulfanylbenzyl)ethylamino]nicotinic acid

HRID 545978Notes

Reaction equation

HRID 545978 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:6][CH:5]=1.[OH-].[K+]>C1COCC1.O>[CH2:21]([S:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][CH2:12][CH2:11][NH:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:28])=[O:2])=[CH:5][N:6]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 672068256-[(2-Benzylsulfanylbenzyl)ethylamino]nicotinic Acid Methyl Ester

Product 1

HCID 672060106-[(2-Benzylsulfanylbenzyl)ethylamino]nicotinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the ester of Example 6 in THF (0.8 mL) was added a solution of KOH (14 mg, 0.255 mmol) in H2O (0.2 mL). The mixture was stirred at 50° C., then concentrated to remove THF. The aqueous phase was washed with ethyl ether, then the aqueous phase was acidified until pH 3-4 was reached. The acidified solution was extracted with Et2O or EtOAc (3×), dried over MgSO4, filtered and concentrated in vacuo to give a white solid.

Workup

  1. concentrationconcentrated
  2. customto remove THF
  3. washThe aqueous phase was washed with ethyl ether
  4. extractionThe acidified solution was extracted with Et2O or EtOAc (3×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a white solid

Sources & evidence

ORD record
ord-3f996e50fffe4c389e2fa534e6c5533a
Source dataset
uspto-grants-2011_05
Patent number
US07935825B2

Reaction notes

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