4-Iodoaniline → 1-(4-iodophenyl)-1H-pyrrole-3-carbaldehyde

HRID 643024

Reaction equation

HRID 643024 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C[O:10][CH:11]1[CH:15]([CH:16]=O)[CH2:14][CH:13](OC)O1>CC(O)=O>[I:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH:13]=[CH:14][C:15]([CH:11]=[O:10])=[CH:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 108934-IodoanilineHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde

Product 1

HCID 866140071-(4-iodophenyl)-1H-pyrrole-3-carbaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-iodoaniline (0.684 g, 3.12 mmol) and 2,5-dimethoxy-3-tetrahydrofurancarboxaldehyde (90%, 0.492 mL, 3.12 mmol) in HOAc (10 mL) was stirred at 90° C. for 1 h. The solvent was removed in vacuo. The residue was partitioned between EtOAc and H2O. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, and concentrated in vacuo to give 1-(4-iodophenyl)-1H-pyrrole-3-carbaldehyde (0.927 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was partitioned between EtOAc and H2O
  3. customThe organic phase was separated
  4. washwashed with 5% NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a41ca07ef2244b9a8e867d12f05f0add
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Linked notes

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