Water → HCID 66785817, compound

HRID 635375Notes

Reaction equation

HRID 635375 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([CH:19]=O)[C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].O.[N+:27]([CH3:30])([O-:29])=[O:28]>>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([CH:19]=[CH:30][N+:27]([O-:29])=[O:28])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 10107997HCID 10107997, compound

Product 1

HCID 66785817HCID 66785817, compoundYield 90%

Procedure

To a solution of 1- benzenesulphonyl-1H-indole-4-carboxaldehyde (1.9 g, 6.6 mmol) in nitromethane (12 ml) was added ammonium acetate (205 mg, 2.7 mmol) and the resulting mixture was refluxed for 2 hours. Water (50 ml) was added and products were extracted with ethyl acetate (2×100 ml). The combined organic phases were washed with brine (1×30 ml), dried (MgSO4) and concentrated. Flash chromatography (silica gel, dichloromethane-hexane, 75:25) of the residue gave 1.95 g (90%) of the title compound as a pale yellow solid; δH (250 MHz, CDCl3) 8.27 (1H, d, J=13.7 Hz), 8.14 (1H, d, J=8.2 Hz), 7.92-7.87 (2H, m), 7.75 (1H, d, J=3.7 Hz), 7.65 (1H, d, J=13.7 Hz), 7.62-7.34 (5H, m), 6.89 (1H, dd, J=3.7 and 0.9 Hz); m/z (CI) 299 (M++1).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hours
  2. extractionproducts were extracted with ethyl acetate (2×100 ml)
  3. washThe combined organic phases were washed with brine (1×30 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1880c2fa28c9415da31824e455fbd262
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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