Sodium Carbonate → 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-6-one

HRID 3568Notes

Reaction equation

HRID 3568 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][C:16]([O:18]CC)=O)([O-])=O.O.O.[Cl-].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.Cl>[CH:6]1[C:5]2[N:10]3[CH:14]=[CH:13][CH:12]=[C:11]3[CH2:15][C:16](=[O:18])[NH:1][C:4]=2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21226388Chloride dihydrateHCID 861831311-(2-Nitrophenyl)-2-pyrroleacetic acid, ethyl ester

Product 1

HCID 123593406,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-6-oneYield 100.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 0.8 mmol of 1-(2-nitrophenyl)-2-pyrroleacetic acid, ethyl ester in 3 ml of ethanol is added stannus chloride dihydrate (SnCl2.2H2O) in 2 ml of concentrated hydrochloric acid (with cooling in water bath). The mixture is stirred at room temperature for 5 hours and chilled in an ice bath. To the mixture is added slowly saturated sodium carbonate solution. The solid which precipitates is filtered and the solid washed with water and then extracted with ethyl acetate. The ethyl acetate extract is dried (Na2SO4) and the solvent removed to give 0.16 g of solid which is triturated with ether to give 0.11 g of product as an off-white solid.

Workup

  1. temperaturechilled in an ice bath
  2. customThe solid which precipitates
  3. filtrationis filtered
  4. washthe solid washed with water
  5. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. dry with materialis dried (Na2SO4)
  8. customthe solvent removed

Sources & evidence

ORD record
ord-71b7c25325774f938eaad758b0324b5c
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Reaction notes

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