HCID 22145918, compound → HCID 22145707, compound

HRID 1489676Notes

Reaction equation

HRID 1489676 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[NH:11][C:12](=[O:27])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:14]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[NH:11][C:12](=[O:27])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)[CH:14]=1

Participants

4

Reactant 1

HCID 22145918HCID 22145918, compound

Product 1

HCID 22145707HCID 22145707, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2,6-dichloro-4-hydroxymethylphenyl)-3-cyclopentyloxy-4-methoxybenzamide (4.4 g) in dichloromethane (30 mL) is treated with activated manganese dioxide (6.2 g), and the mixture is stirred at reflux for 24 hours. The mixture is filtered, the filtrate is evaporated, and the resulting residue is subjected to flash chromatography on silica gel, eluting with ethyl acetate, to give N-(2,6-dichloro-4-formylphenyl)-3-cyclopentyloxy-4-methoxybenzamide (2.4 g), m.p. 96°-98° C. [Elemental analysis: C,59.0; H,5.1; N,3.1%; calculated: C,58.8; H,4.7; N,3.4%].

Workup

  1. temperatureat reflux for 24 hours
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4bc69aac6e6e456aa4be32deaf456822
Source dataset
uspto-grants-1997_10
Patent number
US05679696

Reaction notes

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