Tetrahydrofuran → Isopropanol hydrochloride

HRID 2393554Notes

Reaction equation

HRID 2393554 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][CH:11]2[CH2:19][C:18]3[C:13](=[CH:14][C:15]([N+:20]([O-:22])=[O:21])=[CH:16][CH:17]=3)[CH2:12]2)=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:23]1COCC1>>[CH3:23][CH:8]([OH:9])[CH3:4].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:10][CH:11]2[CH2:19][C:18]3[C:13](=[CH:14][C:15]([N+:20]([O-:22])=[O:21])=[CH:16][CH:17]=3)[CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 232983992-((3-Chlorophenyl)carbonyl)amino-5-nitroindane

Product 2

HCID 21912024Isopropanol hydrochlorideHCID 232983962-((3-Chlorophenyl)methyl)amino-6-nitroindane

Conditions

Temperature
0 °C

Procedure

To 2-((3-chlorophenyl)carbonyl)amino-6-nitroindane (2.2 g, 7.0 mmol) in THF (75 ml) was added BH3 -THF (1.0M, 35 ml, 35 mmol) dropwise. The mixture was refluxed for 12 hr, cooled to 0° C., quenched with 4N HCl (60 ml), and refluxed for 1 hr. The resulting solution was evaporated to an oil, made basic with 50% NaOH, and extracted with methylene chloride (3×20 ml). The combined extracts were washed with water, dried over MgSO4, filtered and concentrated to an oil. Treatment with IPA/HCl yielded 2-((3-chlorophenyl)methyl)amino-6-nitroindane: (2.1 g, 88% two steps); m.p. 234°-237° C.

Workup

  1. temperatureThe mixture was refluxed for 12 hr
  2. customquenched with 4N HCl (60 ml)
  3. temperaturerefluxed for 1 hr
  4. customThe resulting solution was evaporated to an oil
  5. extractionextracted with methylene chloride (3×20 ml)
  6. washThe combined extracts were washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-35e158849b064e73b516fd712c79d302
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

Loading…