HCID 22145918, compound → HCID 22145707, compound

HRID 1994317Notes

Reaction equation

HRID 1994317 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-e2d9847b468848019010f4fbd31bf683
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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