Ethyl Acetate → HCID 22667747, compound

HRID 2230045Notes

Reaction equation

HRID 2230045 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13](O)=[O:14])[CH:7]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+].CCOC(C)=O>C(O)C.O.Cl>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([NH:16][C:13](=[O:14])[CH:9]3[CH2:10][CH2:11][CH2:12][N:8]32)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 22667726HCID 22667726, compound

Product 1

HCID 22667747HCID 22667747, compoundYield 60.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of N-(5-bromo-2-nitro-phenyl)-pyrrolidine-2-carboxylic acid (6g, 23 mmol) and tin(II) chloride dihydrate (16.5 g, 73 mmol) in ethanol (200 ml), water (30 ml) and concentrated HCl (10 ml) was heated to reflux for 6 hours. After cooling to room temperature, the mixture was diluted with water and was adjusted to pH 9 with 2N aqueous sodium hydroxide solution. After addition of EtOAc, the precipitated tin hydroxide was filtered off. The layers were separated and the organic layer was washed with water, then brine, dried (MgSO4) and evaporated to afford 8-bromo-1,2,3,3a-tetrahydro-5H-pyrrolo(1,2-a)quinoxalin-4-one (3.7 g, 60%), which was used without further purification.

Workup

  1. temperatureto reflux for 6 hours
  2. filtrationthe precipitated tin hydroxide was filtered off
  3. customThe layers were separated
  4. washthe organic layer was washed with water
  5. dry with materialbrine, dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-3ed7353de6b54c008de1bf867095df11
Source dataset
uspto-grants-2002_07
Patent number
US06423699B1

Reaction notes

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