Methanol → methyl 2-[(2-nitrophenyl)amino]benzoate

HRID 1747426Notes

Reaction equation

HRID 1747426 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])([O-:3])=[O:2].OS(O)(=O)=O.O.[OH-].[Na+].[CH3:28]O>>[CH3:28][O:14][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=1[NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 101319Anthranilic acid, N-o-nitrophenyl-

Product 1

HCID 292094methyl 2-[(2-nitrophenyl)amino]benzoateYield 80%

Procedure

2-(2-Nitro-phenylamino)-benzoic acid (560 mg, 2.2 mmol) is dissolved in methanol (10 mL) and concentrated H2SO4 (0.16 mL, 98%) is added into it. The mixture is then refluxed for 60 hr. After it is cooled down to room temperature, 100 mL of water is added and the pH of this solution is adjusted to pH 7 by adding 1.0 M NaOH aqueous solution. An orange solid is formed and it is filtered and rinsed with more water. Air drying of this orange solid affords 470 mg (80%) of 2-(2-Nitro-phenylamino)-benzoic acid methyl ester.

Workup

  1. temperatureThe mixture is then refluxed for 60 hr
  2. customAn orange solid is formed
  3. filtrationit is filtered
  4. washrinsed with more water
  5. customAir drying of this orange solid

Sources & evidence

ORD record
ord-93fa416c4c91411d9c07b10b73dc0911
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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