Sodium Hydroxide → 1-phenyl-1H-pyrrol-3-amine

HRID 1802055Notes

Reaction equation

HRID 1802055 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=1)([O-])=O.[OH-].[Na+]>CCOC(C)=O>[C:9]1([N:6]2[CH:7]=[CH:8][C:4]([NH2:1])=[CH:5]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21783328HCID 21783328, compound

Product 1

HCID 108666071-phenyl-1H-pyrrol-3-amineYield 93.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-nitro-1-phenyl-1H-pyrrole (410 mg, 2.18 mmol) and SnCl2 dihydrate (2.00 g, 8.86 mmol) in EtOAc (15 mL) was stirred at 80 C for 3 h. Aqueous 1N NaOH was added to bring pH to 12. The mixture was filtered through celite. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 1-phenyl-1H-pyrrol-3-amine as a solid (323 mg).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95950448fdee49ce89ff51fbb30b3f6f
Source dataset
uspto-grants-2013_01
Patent number
US08349860B2

Reaction notes

Loading…