Lithium Hydroxide → 7,7-Dimethyl-5-(2-nitrophenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid

HRID 468672Notes

Reaction equation

HRID 468672 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:7][N:6]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])(=[O:10])=[O:9])[CH2:5][C:4]2[CH:20]=[C:21]([C:23]([O:25]CC)=[O:24])[S:22][C:3]1=2.[Li+].[OH-]>C1COCC1>[CH3:1][C:2]1([CH3:28])[CH2:7][N:6]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])(=[O:10])=[O:9])[CH2:5][C:4]2[CH:20]=[C:21]([C:23]([OH:25])=[O:24])[S:22][C:3]1=2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66932174Ethyl 7,7-dimethyl-5-(2-nitrophenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate

Product 1

HCID 669317517,7-Dimethyl-5-(2-nitrophenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7,7-dimethyl-5-(2-nitrophenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate (32.6 g, 76.8 mmol) in THF (853 mL) was added 1.0 M aqueous LiOH (307 mL, 307 mmol) and the reaction mixture stirred overnight at room temperature. The solution was concentrated and the residue dissolved in water (100 mL) and neutralized with 1.0 M aqueous HCl (307 mL). The resulting precipitate was collected via vacuum filtration to afford white solid (29 g, 95%). LCMS (FA) ES+ 397; 1H NMR (400 MHz, DMSO) δ 13.04 (s, 1H), 8.08 (dd, J=7.6, 1.6 Hz, 1H), 8.02 (dd, J=7.7, 1.5 Hz, 1H), 7.95-7.86 (m, 2H), 7.49 (s, 1H), 4.36 (s, 2H), 3.40 (s, 2H), 1.28 (s, 6H).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue dissolved in water (100 mL)
  3. filtrationThe resulting precipitate was collected via vacuum filtration

Sources & evidence

ORD record
ord-679ec1914e0049e0b6eb4e97b741e9d1
Source dataset
uspto-grants-2014_01
Patent number
US08624040B2

Reaction notes

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