3-Nitrobenzoic acid → Methyl 3-nitrobenzoate

HRID 1658187Notes

Reaction equation

HRID 1658187 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[CH3:13]N(N=O)C(N)=O.[OH-].[K+]>COCCOC.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([O:9][CH3:13])=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 84973-Nitrobenzoic acidHCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium Hydroxide

Product 1

HCID 69260Methyl 3-nitrobenzoateYield 149.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.00 grams (6 millimoles) of m-nitrobenzoic acid and 2.4 grams (2.4 millimoles) of N-methyl,N-nitrosourea were dissolved in 25 milliliters of a 5:1 mixture of 1,2-dimethoxyethane and water. 40 milliliters of 0.6 N potassium hydroxide was added in a dropwise manner while the mixture was held at 0°C. in an ice bath. The solution was extracted with ether (4×50 milliliters) and the water layer (pH 10) was saved. The ether layer was dried (MgSO4) and workup gave 0.65 grams of methyl m-nitrobenzoate, melting point 71°-72°C. The water layer gave 0.25 grams of unreacted acid. Yield, based on consumed acid, was approximately 85 percent.

Workup

  1. customwas held at 0°C. in an ice bath
  2. extractionThe solution was extracted with ether (4×50 milliliters)
  3. dry with materialThe ether layer was dried (MgSO4) and workup

Sources & evidence

ORD record
ord-a3098aa84a624c28bac6bf1f8b1c1bc2
Source dataset
uspto-grants-1976_06
Patent number
US03963698

Reaction notes

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