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

HRID 1940765Notes

Reaction equation

HRID 1940765 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-27d8fe36a3834ec3a58b712d9bca0ab6
Source dataset
uspto-grants-1997_12
Patent number
US05700796

Reaction notes

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