Hydrochloric Acid → HCID 19780724, compound

HRID 2081805Notes

Reaction equation

HRID 2081805 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([CH2:16][N+:17]([O-:19])=[O:18])(=[O:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)C.Cl>C(O)C>[N+:17]([CH2:16][S:13]([C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][CH2:5][CH2:6]2)(=[O:14])=[O:15])([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19780710HCID 19780710, compound

Product 1

HCID 19780724HCID 19780724, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Acetyl-5-(nitromethylsulphonyl)indoline (5.41 g, 19 mM) was added in one portion to a boiling mixture of 2M hydrochloric acid (60 ml) and ethanol (20 ml). The mixture was heated at reflux until a clear solution formed, and then for a further 5 minutes. The hot reaction mixture was poured into ice-cold saturated sodium hydrogen carbonate solution (100 ml) and then extracted with ethyl acetate. The combined extracts were dried (MgSO4) and the solvent was removed by evaporation. The resultant yellow oil was purified by vacuum flash chromatography on silica, eluting with dichloromethane, to give 5-(nitromethylsulphonyl)indoline as a pale yellow solid, m.p. 139° C.; NMR(d6 -DMSO): 3.0(2H,t), 3.6(2H,t), 6.3(2H,s), 6.5(2H,s), 6.9(1H,s), 7.4-7.5(2H,m); microanalysis, found: C,44.5; H,4.1; N,11.4%; C9H10N2O4S requires: C,44.6; H,4.1; N,11.6%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux until a clear solution
  3. customformed
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent was removed by evaporation
  7. customThe resultant yellow oil was purified by vacuum flash chromatography on silica
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-25355e77761a4514aac8b39e0da904ba
Source dataset
uspto-grants-1993_02
Patent number
US05185452

Reaction notes

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