2-(4-Nitrophenyl)indolizine → 2-(4-Aminophenyl)indolizine

HRID 1965839Notes

Reaction equation

HRID 1965839 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[N:17]([CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:6][CH:5]=1)([O-])=O.[BH4-].[Na+]>CCO.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[C:12]3[N:17]([CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 2439792-(4-Nitrophenyl)indolizineHCID 4311764Sodium borohydride

Product 1

HCID 157499552-(4-Aminophenyl)indolizineYield 53%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-nitrophenyl)indolizine (0.2 g, 0.84 mmol) and Cu(OAc)2 (0.16 g, 0.88 mmol) in EtOH (50 mL) was added NaBH4 (0.64 g, 16.8 mmol). The resulting mixture was stirred at room temperature for 3 hrs and concentrated in vacuo. The residue was dissolved in H2O (20 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried (MgSO4), filtered. The filtrate was concentrated in vacuo to give a solid (0.092 g, 53%). 1H NMR (CDCl3, 400 MHz) δ: 7.87 (dd, J=6.8, 1.2 Hz, 1H), 7.44-7.95 (m, 3H), 7.31 (d, J=8.4 Hz, 1H), 6.73 (d, J=8.4 Hz, 2H), 6.59-6.64 (m, 2H), 6.42 (td, J=6.8, 1.2 Hz, 1H), 3.67 (br s, 2H). MS: m/z=209 (M+H+).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in H2O (20 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4a719643db7f48d695df9c6035527d15
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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