HCID 131733469, compound → HCID 53964687, compound

HRID 2278402Notes

Reaction equation

HRID 2278402 reaction equation
[Br:1][C:2]1[C:7]([CH2:8][CH3:9])=[CH:6][CH:5]=[C:4]([N+]([O-])=O)[C:3]=1[CH:13]=[CH:14][N:15]1CCCC1>CC(O)=O.O.C([O-])([O-])=O.[Na+].[Na+].[Fe]>[Br:1][C:2]1[C:7]([CH2:8][CH3:9])=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:13]=[CH:14][NH:15]2

Participants

6

Reactant 1

HCID 131733469HCID 131733469, compound

Product 1

HCID 53964687HCID 53964687, compoundYield 12%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of crude 1-[2-(2-bromo-3-ethyl-6-nitro-phenyl)-vinyl]-pyrrolidine from Step 3 in 80 mL of AcOH was added in one portion to a refluxing suspension of iron (13 g) in 50 mL of AcOH. The resultant mixture was refluxed for 2 hrs. After cooling, the mixture was diluted with water and neutralized with Na2CO3, and extracted 3 times with EtOAc. The combined organic phases were concentrated and purified by silica gel column chromatography and preparative HPLC to yield the title compound (1.5 g, 12% from 6-ethyl-2-methyl-3-nitro-phenylamine).

Workup

  1. temperatureAfter cooling
  2. extractionextracted 3 times with EtOAc
  3. concentrationThe combined organic phases were concentrated
  4. custompurified by silica gel column chromatography and preparative HPLC

Sources & evidence

ORD record
ord-4fc6ec3fdd52464f9d85f0e7d4be7f63
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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