2-(4-Nitrobenzoyl)-1-(2-trimethylsilylethoxymethyl)pyrrole → HCID 22624249, compound

HRID 279053Notes

Reaction equation

HRID 279053 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]([C:10]2[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([C:10]2[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 226242202-(4-Nitrobenzoyl)-1-(2-trimethylsilylethoxymethyl)pyrrole

Product 1

HCID 22624249HCID 22624249, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Iron powder (0.52 g) was added in three portions to a stirred solution of 2-(4-nitrobenzoyl)-1-(2-trimethylsilylethoxymethyl)pyrrole (0.59 g. 1.7 mM) in acetic acid at 65° C. Heating was continued for 2 hours and solvent was evaporated and the residue partitioned between EtOAc and water. The organic layer was washed with water, dried (Mg SO4) and evaporated, to give 2-(4-aminobenzoyl)-1-(2-trimethylsilylethoxymethyl)pyrrole as an oil (0.5 g). MS: 317 (MH+). NMR: −0.18 (9H, s); 0.74 (2H, t) 3.38 (2H, t); 5.64 (2H, s); 5.95 (2H, s); 6.16 (1H, m); 6.59 (2H, d) 6.6 (1H, m); 7.3 (1H, m); 7.57 (2H, d).

Workup

  1. temperatureHeating
  2. customsolvent was evaporated
  3. customthe residue partitioned between EtOAc and water
  4. washThe organic layer was washed with water
  5. dry with materialdried (Mg SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-4523bb3802694b89ba97104c13763c6f
Source dataset
uspto-grants-2002_03
Patent number
US06362191B1

Reaction notes

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