2-Nitroaniline → 1-(2-Nitrophenyl)pyrrole

HRID 556729Notes

Reaction equation

HRID 556729 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].CO[CH:13]1[CH2:17][CH2:16][CH:15](OC)O1>C(O)(=O)C>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[N:6]1[CH:13]=[CH:17][CH:16]=[CH:15]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 69462-NitroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 5206111-(2-Nitrophenyl)pyrroleYield 96.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.37 g (9.9 mmol) 2-nitro-anilin and 1.3 ml (11 mmol) of 2,5-dimethoxy-tetrahydrofuran was refluxed for 1 hour in 20 ml acetic acid. The reaction mixture was evaporated and the residue was diluted in EtOAc and washed with water, NaHCO3 (sat.), water, and then dried over Na2SO4. The solvent was evaporated and 1.8 g (96%) of 1a was obtained as an oil.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted in EtOAc
  3. washwashed with water, NaHCO3 (sat.), water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a93cac501d0d44949b59d6ec104728f6
Source dataset
uspto-grants-2011_11
Patent number
US08058306B2

Reaction notes

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