Hydrochloric Acid → 7-(2-Cyano-4-nitrobenzenesulfonamido)-4-methyl-3-coumarinylacetic acid

HRID 2369750Notes

Reaction equation

HRID 2369750 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[S:12]([NH:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([CH3:32])=[C:21]([CH2:27][C:28]([O:30]C)=[O:29])[C:22](=[O:26])[O:23]2)=[CH:18][CH:17]=1)(=[O:14])=[O:13])#[N:2].Cl>C1COCC1.O>[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[S:12]([NH:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([CH3:32])=[C:21]([CH2:27][C:28]([OH:30])=[O:29])[C:22](=[O:26])[O:23]2)=[CH:18][CH:17]=1)(=[O:14])=[O:13])#[N:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86668468Methyl 7-(2-cyano-4-nitrobenzenesulfonamido)-4-methylcoumarin-3-acetate

Product 1

HCID 866684697-(2-Cyano-4-nitrobenzenesulfonamido)-4-methyl-3-coumarinylacetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 2a was dissolved in THF (3.5 ml), lithium hydroxide•monohydrate (22.2 mg, 0.53 mmol, 7.6 equivalents) dissolved in H2O (3.5 ml) was added under cooling on ice, and the mixture was stirred. After 30 min, the reaction mixture was warmed to room temperature and further stirred. After 3 hr, the disappearance of the starting materials was confirmed by TLC and the reaction mixture was acidified with 5% HCl and extracted with CHCl3. The organic layer was washed with saturated brine, and dried over Na2SO4. The solvent was evaporated, and the residue was purified by silica gel column chromatography (eluate: 1% acetic acid-containing CHCl3:MeOH=20:1) (compound 3a: 29.6 mg, 0.07 mmol, 95%).

Workup

  1. additionwas added
  2. temperatureunder cooling on ice
  3. waitAfter 3 hr
  4. extractionextracted with CHCl3
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography (eluate: 1% acetic acid-containing CHCl3:MeOH=20:1) (compound 3a: 29.6 mg, 0.07 mmol, 95%)

Sources & evidence

ORD record
ord-f2078aaed8404120b4cc835436305a6c
Source dataset
uspto-grants-2014_04
Patent number
US08709721B2

Reaction notes

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