Calcium Chloride → N-(3-amino-5-pyrrol-1-yl-phenyl)acetamide

HRID 64109Notes

Reaction equation

HRID 64109 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:15][C:16](=[O:18])[CH3:17])[CH:7]=[C:8]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[CH:9]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:15][C:16](=[O:18])[CH3:17])[CH:7]=[C:8]([N:10]2[CH:11]=[CH:12][CH:13]=[CH:14]2)[CH:9]=1

Participants

6

Reactant 2

HCID 5284359Calcium ChlorideHCID 89500059HCID 89500059, compound

Product 1

HCID 89500087N-(3-amino-5-pyrrol-1-yl-phenyl)acetamideYield 87%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(3-nitro-5-pyrrol-1-yl-phenyl)acetamide (7.51 g, 30.61 mmol) in ethanol (100 ml), were added iron powder (4.273 g, 76.53 mmol, 2.5 eq.) and a solution of calcium chloride (8.49 g, 76.53 mmol, 2.5 eq.) in water (100 ml). The mixture was stirred at 80° C. for 2 h and then filtered through a pad of celite. The celite pad was washed with ethyl acetate (200 ml) and the combined organic layer was washed with water (100 ml) and brine (25 ml). The solvent was evaporated and the residue was purified by column chromatography (20% ethyl acetate in hexanes) to give the compound in 87% yield (5.7 g). 1H NMR (300 MHz, DMSO-d6): δ 9.9 (s, 1H), 8.25 (s, 1H), 7.8 (d, 1H), 7.6 (s, 1H), 7.05 (d, 1H), 6.8 (s, 1H), 6.5 (m, 1H), 6.3 (m, 1H), 5.15 (s, 2H), 2.02 (s, 3H).

Workup

  1. filtrationfiltered through a pad of celite
  2. washThe celite pad was washed with ethyl acetate (200 ml)
  3. washthe combined organic layer was washed with water (100 ml) and brine (25 ml)
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography (20% ethyl acetate in hexanes)
  6. customto give the compound in 87% yield (5.7 g)

Sources & evidence

ORD record
ord-ea58148aef954cebb095fa331d348f68
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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