Ammonium Hydroxide → 2-Amino-5-bromobenzamide

HRID 2079290Notes

Reaction equation

HRID 2079290 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-bromobenzamide

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 with CH2Cl2 yielding 35.4 g (71.2%) of 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 with CH2Cl2 yielding 35.4 g (71.2%) of 2-amino-5-bromo-benzamide

Sources & evidence

ORD record
ord-763794cc0bd44ea589a3a5e5afca33d0
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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