Water → HCID 66868258, compound

HRID 1909858Notes

Reaction equation

HRID 1909858 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-])=O)=[C:6]([CH:18]=1)[CH:7]=[C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10](=[O:17])[O:9]1.[Cl-].[NH4+].O>C(O)C>[NH2:19][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:18][C:6]=1[CH:7]=[C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10](=[O:17])[O:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 66868239HCID 66868239, compound

Product 1

HCID 66868258HCID 66868258, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(5-chloro-2-nitrobenzylidene)-2-benzofuran-1(3H)-one (808 mg), reduced iron (750 mg), ammonium chloride (72 mg), water (2.5 mL), and ethanol (25 mL) was stirred at 80° C. for 4 hours. The reaction mixture was filtered using Celite and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 3-(2-amino-5-chlorobenzylidene)-2-benzofuran-1(3H)-one (466 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-18b8b613a2f84be6bfc066296bc6fc58
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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