Isatoic Anhydride → Anthranilamide

HRID 2079304Notes

Reaction equation

HRID 2079304 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)O[C:2]2=[O:3].[NH4+:13].[OH-]>>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH2:13])=[O:3]

Participants

3

Reactant 2

HCID 8359Isatoic AnhydrideHCID 14923Ammonium Hydroxide

Product 1

HCID 6942AnthranilamideYield 32.7%

Procedure

Isatoic anhydride (40 g, 245 mmol) was suspended in 650 mL 1 N NH4OH (2.5 equiv) and stirred at room temperature for 3 days. The precipitate was filtered and washed with water. The product was then dissolved in THF, filtered, and concentrated to dryness. The product was dried by azeotropic distillation with toluene and washed with CH2Cl2 to yield 10.9 g (32.7%) of 2-amino-benzamide.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. dissolutionThe product was then dissolved in THF
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. dry with materialThe product was dried by azeotropic distillation with toluene
  7. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-4883aab2bd894df8a57bbd1cd286ef31
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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