Isatoic Anhydride → Anthranilamide

HRID 2062219Notes

Reaction equation

HRID 2062219 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-b33bcfc5cd8640acb7639ba97250e8d5
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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