Hydrochloric Acid → N-(4-methoxyphenyl)-4-nitrobenzamide

HRID 2276903Notes

Reaction equation

HRID 2276903 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.O.Cl>N1C=CC=CC=1>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7732P-AnisidineHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 532159N-(4-methoxyphenyl)-4-nitrobenzamideYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

After adding 4-nitrobenzoyl chloride (34, 7.534 g, 185.57 mmol) to p-anisidine (33, 5.00 g, 40.60 mmol) dissolved in pyridine (50 mL), the reaction mixture was heated for 2 hours at 100° C. After adding water and aqueous 4 N HCl (300 mL), extracting with ethyl acetate and removing water using sodium sulfate, column chromatography yielded the target compound N-(4-methoxyphenyl)-4-nitrobenzamide (36, 8.594 g, 78%).

Workup

  1. extractionextracting with ethyl acetate
  2. customremoving water

Sources & evidence

ORD record
ord-7e6b970951ca4c8594fda00a686bffaf
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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