Chlorosuccinimide → N-(9-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)-N-hydroxy urea

HRID 653684Notes

Reaction equation

HRID 653684 reaction equation
[CH:1]1([N:13]([OH:17])[C:14]([NH2:16])=[O:15])[C:5]2=[CH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]2[CH2:3][CH2:2]1.[Cl:18]N1C(=O)CCC1=O>C1COCC1>[Cl:18][C:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[N:4]2[CH2:3][CH2:2][CH:1]([N:13]([OH:17])[C:14]([NH2:16])=[O:15])[C:5]=12

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 10177000N-(2,3-Dihydro-1H-pyrrolo[1,2-a]indol-1-yl)-N-hydroxy urea

Product 1

HCID 19889900N-(9-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)-N-hydroxy urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-(2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)-N-hydroxy urea (from Example 1, 231 mg, 1 mmol) in THF (9 mL) there was added N-chlorosuccinimide (147 mg, 1.1 mmol) and the mixture was stirred at r.t. for 30 minutes as a clear solution resulted. After evaporation to dryness, the residue was partitioned between H2O and EtOAc. The product obtained from evaporation of the organic fraction was chromatographed on a short column of silica gel, eluting with 5% EtOH in CH2Cl2 to afford a solid which on trituration in Et2O and filtration afforded the title compound as a white solid, m.p.: 192° C. (dec).

Workup

  1. customresulted
  2. customAfter evaporation to dryness
  3. customthe residue was partitioned between H2O and EtOAc
  4. customThe product obtained from evaporation of the organic fraction
  5. customwas chromatographed on a short column of silica gel
  6. washeluting with 5% EtOH in CH2Cl2
  7. customto afford a solid which on trituration in Et2O
  8. filtrationfiltration

Sources & evidence

ORD record
ord-b22511a789ff491fb49fb0a56b0b6880
Source dataset
uspto-grants-1992_07
Patent number
US05128364

Reaction notes

Loading…