Indoline → HCID 9431961, compound

HRID 652406Notes

Reaction equation

HRID 652406 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH2:10]1[CH2:16][S:13](=[O:15])(=[O:14])[O:12][CH2:11]1>C(#N)C>[N:1]1([CH2:11][CH2:10][CH2:16][S:13]([OH:15])(=[O:14])=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10328IndolineHCID 14264Propane sultone

Product 1

HCID 9431961HCID 9431961, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of dihydroindole (4.76 g, 40 mmole) and 1,3-propane sultone (4.88 g, 40 mmole) in 50 ml reagent grade acetonitrile was heated under a nitrogen atmosphere and refluxed overnight. After cooling to room temperature, then to ice bath temperature, the resulting white solid was filtered and washed with cold acetonitrile. The yield was 8.1 g (84%), and the product had a melting point of greater then 200° C. Nuclear magnetic resonance (NMR) and elemental analysis showed the product to be consistent with the assigned structure. NMR (D2O): 7.45 (s, 4H), 2.8-4.0 (m, 8H), 2.2 (t, 2H).

Workup

  1. temperaturewas heated under a nitrogen atmosphere
  2. temperaturerefluxed overnight
  3. filtrationto ice bath temperature, the resulting white solid was filtered
  4. washwashed with cold acetonitrile
  5. custom200° C

Sources & evidence

ORD record
ord-62258a81e141476c90f31957174c36f4
Source dataset
uspto-grants-1987_06
Patent number
US04672029

Reaction notes

Loading…