HCID 13477606, compound → HCID 13477607, compound

HRID 370851Notes

Reaction equation

HRID 370851 reaction equation
[C:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([N+:16]([O-])=O)[CH:13]=[CH:14][CH:15]=2)=[CH:6][C:5]=1[OH:21])(=[O:3])[CH3:2]>C(O)C.[Fe]>[C:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[NH2:16])=[CH:6][C:5]=1[OH:21])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 13477606HCID 13477606, compound

Product 1

HCID 13477607HCID 13477607, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-[(4-acetyl-3-hydroxyphenoxy)methyl]nitrobenzene (10.2 g) and iron powder (10.4 g) in ethanol (150 ml, saturated with anhydrous HCl) is stirred at room temperature for 15 hours. After removal of excess iron and concentration in vacuo, the residue is partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic phase is filtered through a Florisil column with the aid of dichloromethane. Concentration gives 7.4 g of product (81% yield) m.p. 153°-154° C.

Workup

  1. customAfter removal of excess iron and concentration in vacuo
  2. customthe residue is partitioned between dichloromethane and saturated sodium bicarbonate solution
  3. filtrationThe organic phase is filtered through a Florisil column with the aid of dichloromethane
  4. concentrationConcentration

Sources & evidence

ORD record
ord-7be6252bdd3c406797d21cecf9f3ce8b
Source dataset
uspto-grants-1985_07
Patent number
US04528392

Reaction notes

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