Ammonium Hydroxide → 4-Methyl-2-nitrobenzamide

HRID 1469756Notes

Reaction equation

HRID 1469756 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH4+:20].[OH-]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:20])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 2550274-Methyl-2-nitrobenzoic acid

Product 1

HCID 132443694-Methyl-2-nitrobenzamideYield 160.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-methyl-2-nitrobenzoic acid (1.0 g, 5.52 mmol) in toluene (5 mL) was added oxalyl chloride (1.04 g, 8.28 mmol) at 0° C. and the reaction mixture was stirred at rt for 2 h. Then the reaction mixture was concentrated and the concentrate was dissolved in THF (5 mL). Then NH4OH (1.93 g, 55.20 mmol) was added to the solution at 0-5° C. and the reaction mixture was stirred at rt for 4 h before it was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated to afford 1.6 g of the desired product. 1H NMR (300 MHz, DMSO-d6): δ 8.08 (br s, 1H), 7.79 (s, 1H), 7.62 (br s, 1H), 7.57-7.50 (m, 2H), 2.41 (s, 3H).

Workup

  1. concentrationThen the reaction mixture was concentrated
  2. dissolutionthe concentrate was dissolved in THF (5 mL)
  3. stirringthe reaction mixture was stirred at rt for 4 h before it
  4. customwas quenched with water
  5. extractionwas extracted with EtOAc
  6. washThe organic layer was washed with brine
  7. customseparated
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-356b990816db44e093bb45f3d85d6216
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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