Hydrochloric Acid → 2,3-Dihydro-1-hydroxamino-1H-pyrrolo[1,2-a]indole

HRID 653682Notes

Reaction equation

HRID 653682 reaction equation
[N:1](=[C:3]1[C:7]2=[CH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4]1)[OH:2].Cl>C1COCC1.CCO>[NH:1]([CH:3]1[C:7]2=[CH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4]1)[OH:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 85213005HCID 85213005, compound

Product 1

HCID 107501202,3-Dihydro-1-hydroxamino-1H-pyrrolo[1,2-a]indole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of the oxime from Step 1 (2.5 g, 13.4 mmol) in THF (30 mL) and EtOH (30 mL), at 0° C. there was added pyridine-borane complex (3.12 g, 33.6 mmol) and then, slowly, 12N aqueous HCl (3.9 mL, 47 mmol). The mixture was stirred at 0° C. for 15 minutes, then at r.t. for 20 hours. The solvents were evaporated and the residue dissolved in H2O (100 mL) and extracted with EtOAc (2×20 mL). The aqueous fraction was then brought to pH 8 with 2.5N aqueous NaOH and the precipitate filtered to afford the title compound as a white solid, m.p.: 159°-161° C.

Workup

  1. additionat 0° C. there was added pyridine-borane complex (3.12 g, 33.6 mmol)
  2. waitat r.t. for 20 hours
  3. customThe solvents were evaporated
  4. dissolutionthe residue dissolved in H2O (100 mL)
  5. extractionextracted with EtOAc (2×20 mL)
  6. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-d1a7b5ee42cf49779347fefa3de8c489
Source dataset
uspto-grants-1992_07
Patent number
US05128364

Reaction notes

Loading…