Sodium Hydroxide → 3-methoxy-4-nitro-N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]-N-methylbenzamide

HRID 1005579Notes

Reaction equation

HRID 1005579 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32])[C:6]([N:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[CH3:9])=[O:7].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32])[C:6]([N:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 220107713-methoxy-4-nitro-N-[2-(5-ethoxycarbonylpent-1-yloxy)-4-methylphenyl]-N-methylbenzamide

Product 1

HCID 187914763-methoxy-4-nitro-N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]-N-methylbenzamideYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-methoxy-4-nitro-N-[2-(5-ethoxycarbonylpent-1-yloxy)-4-methylphenyl]-N-methylbenzamide (7.6 g) in ethanol (76 ml) was treated with 1 N sodium hydroxide solution (33 ml) at ambient temperature and the mixture was stirred at the same temperature for 6 hours. The reaction was quenched by the dropwise addition of 1 N hydrochloric acid (35 ml). The mixture was concentrated and the residue was dissolved in a mixture of ethyl acetate and 1 N hydrochloric acid. The extracted organic layer was washed with brine and dried over magnesium sulfate. The suspension was filtered and the solvent was removed by evaporation to give 3-methoxy-4-nitro-N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]-N-methylbenzamide (7.1 g) as an oil.

Workup

  1. customThe reaction was quenched by the dropwise addition of 1 N hydrochloric acid (35 ml)
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in a mixture of ethyl acetate and 1 N hydrochloric acid
  4. washThe extracted organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe suspension was filtered
  7. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-5987305824104f4c97bc0c8503d80798
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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