Ammonium Acetate → HCID 10751185, compound

HRID 2288017Notes

Reaction equation

HRID 2288017 reaction equation
[Cl:1][C:2]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:5]2[C:6](=O)[O:7]C(=O)[NH:9][C:4]=2[CH:3]=1.C([O-])(=O)C.[NH4+:21]>C(O)(=O)C>[NH2:9][C:4]1[CH:3]=[C:2]([Cl:1])[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:5]=1[C:6]([NH2:21])=[O:7]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 10800240HCID 10800240, compound

Product 1

HCID 10751185HCID 10751185, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

7-Chloro-1,4-dihydro-6-nitro-2H-3,1-benzoxazine-2,4-dione (6.5 g, 26.8 mmol) was suspended in glacial acetic acid (70 mL). Ammonium acetate (6.2 g, 80.6 mmol) was added, and the resulting mixture was heated to 100° C. with stirring for 3 hours. After cooling to room temperature, the brown solution was poured into distilled water (200 mL) to precipitate a yellow solid which was collected by filtration and washed well with water and ether. This material was first air dried, then dried overnight under high vacuum to provide 2-amino-4-chloro-5-nitrobenzamide (4.9 g, 23.0 mmol, 86%): 1H NMR (DMSO-d6): δ 6.92 (s, 1H), 7.49 (br s, 1H), 7.89 (br s, 2H), 8.22 (br s, 1H), 8.53 (s, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe brown solution was poured
  3. distillationinto distilled water (200 mL)
  4. customto precipitate a yellow solid which
  5. filtrationwas collected by filtration
  6. washwashed well with water and ether
  7. customdried
  8. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-54d7047f70df47e79d9ba445ad96d72b
Source dataset
uspto-grants-2000_07
Patent number
US06087368

Reaction notes

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