Water → 4-methoxy-N-(4-nitrophenyl)benzamide

HRID 1402621Notes

Reaction equation

HRID 1402621 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](N)=[CH:5][CH:4]=1.[N+:10]([C:13]1[CH:21]=[CH:20][C:16](C(Cl)=O)=[CH:15][CH:14]=1)([O-:12])=[O:11].[OH2:22].[N:23]1[CH:28]=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:28]([NH:23][C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:21][CH:20]=2)=[O:22])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7732P-AnisidineHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 3460444-methoxy-N-(4-nitrophenyl)benzamide

Procedure

p-Anisidine 1 (1.0 g, 8.1 mmol) was dissolved in anhydrous pyridine (15 ml), 4-nitrobenzoyl chloride 2 (1.5 g, 8.1 mmol) was added. The reaction mixture was allowed to stand at room temperature for 16 hrs. The reaction mixture was poured into water and the precipitate was collected with filtrate under vacuum pressure and washed with 5% sodium bicarbonate (2×10 ml). The product 3 was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ: 10.46 (s, 1H, NH), 8.37 (d, J=5.5 Hz, 2H, H-3′,5′), 8.17 (d, J=6.3 Hz, 2H, H-2′,6′), 7.48 (d, J=6.6 Hz, 2H), 6.97 (d, J=6.5 Hz, 2H), 3.75 (s, 3H, MeO).

Workup

  1. customthe precipitate was collected with filtrate under vacuum pressure
  2. washwashed with 5% sodium bicarbonate (2×10 ml)
  3. customThe product 3 was used in the next step without further purification

Sources & evidence

ORD record
ord-7ed93a9e7c644570af5e64c274dcf5cc
Source dataset
uspto-grants-2014_12
Patent number
US08911707B2

Reaction notes

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