Ammonium Hydroxide → 2-Amino-5-bromobenzamide

HRID 2062205Notes

Reaction equation

HRID 2062205 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6]C(=O)[O:8][C:9](=O)[C:4]=2[CH:3]=1.[NH4+:14].[OH-]>>[NH2:6][C:5]1[CH:12]=[CH:13][C:2]([Br:1])=[CH:3][C:4]=1[C:9]([NH2:14])=[O:8]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 2885615-Bromoisatoic Anhydride

Product 1

HCID 50192712-Amino-5-bromobenzamideYield 71.2%

Procedure

6-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione (56.0 g, 230 mmol) was suspended in 1 N aq. NH4OH (600 mL, 2.6 equivalents), and the suspension was stirred 3 d at room temperature. After filtration, the collected solid was washed with water and subsequently dissolved in tetrahydrofuran. This solution was filtered, evaporated to dryness, and dried by repeated azeotropic distillation with toluene. The solid was suspended in CH2Cl2, filtered, and washed once CH2Cl2 with yielding 35.4 g (71.2%) 2-amino-5-bromo-benzamide.

Workup

  1. filtrationAfter filtration
  2. washthe collected solid was washed with water
  3. dissolutionsubsequently dissolved in tetrahydrofuran
  4. filtrationThis solution was filtered
  5. customevaporated to dryness
  6. customdried
  7. distillationdistillation with toluene
  8. filtrationfiltered
  9. washwashed once CH2Cl2

Sources & evidence

ORD record
ord-58ebecd2871542fdbdecd53dace45ecd
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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