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

HRID 11313Notes

Reaction equation

HRID 11313 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 (3X), 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 (3X)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a white solid

Sources & evidence

ORD record
ord-f2219ebfb64740f68d7e74bc0bbba3d4
Source dataset
uspto-grants-2006_08
Patent number
US07098223B2

Reaction notes

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