Ammonia → HCID 13244367, compound

HRID 606485Notes

Reaction equation

HRID 606485 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C[N:15](C=O)C.C(Cl)(=O)C(Cl)=O.N>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH2:15])=[O:8]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 183715-Methyl-2-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 13244367HCID 13244367, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methyl-2-nitrobenzoic acid (17.0 g, 93.8 mmol) and DMF (0.1 mL) in THF (150 mL) was added dropwise oxalyl chloride (13.1 g, 103 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. This solution was added dropwise to aqueous ammonia (8% aqueous solution, 210 mL) under ice-cooling. The reaction solution was concentrated under reduced pressure to evaporated THF, and the precipitated insoluble material was collected by filtration. The filtered cake was washed with water to give 5-methyl-2-nitrobenzamide as a pale-yellow powder (15.3 g, 90%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customto evaporated THF
  5. filtrationthe precipitated insoluble material was collected by filtration
  6. washThe filtered cake was washed with water

Sources & evidence

ORD record
ord-7cdec4d4f79d417eb3a2a47999b1f258
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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