Hydrochloric Acid → HCID 19780724, compound

HRID 1029763Notes

Reaction equation

HRID 1029763 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 mmol) was added in one portion to a boiling mixture of 2 M 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 flash chromatography on silica (Merck kieselgel Art. 7736), eluting with dichloromethane, to give 5-(nitromethylsulphonyl)indoline as a pale yellow solid, m.p. 139° C.; 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 flash chromatography on silica (Merck kieselgel Art. 7736)
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-3e65c9a836384057a1fe0593513fc2ac
Source dataset
uspto-grants-1992_04
Patent number
US05102905

Reaction notes

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