Water → 5-(Benzyloxy)-4-methoxy-2-nitrobenzamide

HRID 1808504Notes

Reaction equation

HRID 1808504 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1.C(Cl)(=O)C(Cl)=O.O.[OH-].[NH4+:31]>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:6]([C:7]([NH2:31])=[O:8])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 8212205-(Benzyloxy)-4-methoxy-2-nitrobenzoic acid

Product 1

HCID 593618645-(Benzyloxy)-4-methoxy-2-nitrobenzamideYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-methoxy-5-benzyloxy-2-nitrobenzoic acid (10.0 g, 33.3 mmol) in anhydrous THF (100 mL) was added oxalyl chloride (4.90 mL, 56.2 mmol) followed by one drop of anhydrous DMF. The mixture was stirred at RT for 16 h, upon which the mixture was poured into water (300 mL) and ammonium hydroxide (50 mL). A solid was separated out, which was collected by filtration and dried under vacuo. The solid was taken up in refluxing methanol (500 mL) and the insoluble solid was collected via filtration and dried under vacuum to give 4-methoxy-5-benzyloxy-2-nitrobenzamide (6.50 g, 21.5 mmol, 65%). HPLC retention time 6.154 min.

Workup

  1. customA solid was separated out
  2. filtrationwhich was collected by filtration
  3. customdried under vacuo
  4. temperaturein refluxing methanol (500 mL)
  5. filtrationthe insoluble solid was collected via filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-767dfe2344304f219354fa0e4ee80b74
Source dataset
uspto-grants-2013_01
Patent number
US08357693B2

Reaction notes

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