Sodium Hydroxide → HCID 70416267, compound

HRID 1252265Notes

Reaction equation

HRID 1252265 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8](=[O:36])[C:9]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:13]([C:24](=[O:33])[CH2:25][S:26](=[O:32])(=[O:31])[NH:27][CH:28]([CH3:30])[CH3:29])=[C:12]([CH3:34])[NH:11][C:10]=1[CH3:35])(=O)C.[OH-].[Na+]>C(O)C>[OH:4][CH2:5][CH2:6][O:7][C:8](=[O:36])[C:9]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:13]([C:24](=[O:33])[CH2:25][S:26](=[O:32])(=[O:31])[NH:27][CH:28]([CH3:30])[CH3:29])=[C:12]([CH3:34])[NH:11][C:10]=1[CH3:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70416513HCID 70416513, compound

Product 1

HCID 70416267HCID 70416267, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 2.09 g of 1,4-dihydro-5-[(isopropylsulfamoyl)acetyl]-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid 2-acetoxyethyl ester in 20 ml of ethanol was treated dropwise at room temperature with a solution of 0.36 g of sodium hydroxide in 24 ml of ethanol. The dark orange solution obtained was subsequently stirred at room temperature for 1 hour. The ethanol was thereupon evaporated off at 25°-30° under reduced pressure and the residue was dissolved in 20 ml of water. The mixture was acidified cautiously with 2N hydrochloric acid, extracted several times with a mixture of methylene chloride/ethyl acetate (9:1) and the extract was dried over sodium sulfate. After evaporation of the solvent the solid residue was recrystallized from ethanol. There were obtained 1.55 g of 1,4-dihydro-5-[(isopropylsulfamoyl)acetyl]-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid 2-hydroxyethyl ester in the form of pale yellow crystals, m.p. 185°-188°.

Workup

  1. customThe dark orange solution obtained
  2. customThe ethanol was thereupon evaporated off at 25°-30° under reduced pressure
  3. dissolutionthe residue was dissolved in 20 ml of water
  4. extractionextracted several times
  5. additionwith a mixture of methylene chloride/ethyl acetate (9:1)
  6. dry with materialthe extract was dried over sodium sulfate
  7. customAfter evaporation of the solvent the solid residue
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-b04e1ec2c583457593d69138192d0cc4
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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