HCID 22145918, compound → HCID 22145707, compound

HRID 993266Notes

Reaction equation

HRID 993266 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, compound

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; that is prepared as described in Example 9) 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-methoxy-benzamide (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. customthat is prepared
  2. temperatureat reflux for 24 hours
  3. filtrationThe mixture is filtered
  4. customthe filtrate is evaporated
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-817b0a9b58ea4e19bb880942ef5efc4a
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

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