2-Amino-5-methylphenol → 2,2,7-Trimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 2239238Notes

Reaction equation

HRID 2239238 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].Br[C:11]([CH3:16])([CH3:15])[C:12](Br)=[O:13]>ClC(Cl)C>[CH3:15][C:11]1([CH3:16])[C:12](=[O:13])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:9])=[CH:6][C:7]=2[O:8]1

Participants

4

Reactant 2

HCID 760822-Amino-5-methylphenolHCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 594182682,2,7-Trimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 6-amino-m-cresol (10 g, 81.2 mmol) in dichloroethane (100 mL) was treated with 11.1 mL of 2-bromoisobutyryl bromide (89.3 mmol). The reaction was allowed to stir at room temperature for 3 hours, then refluxed overnight. The reaction was cooled to room temperature and filtered through celite. The filtrate and washings were combined and excess solvent removed to yield crude product which was then triturated with hexanes to give pure product as a white solid. MS (electrospray): mass calculated for C11H13NO2, 191.09; m/z found 192.2, [M+H]+.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered through celite
  4. customexcess solvent removed
  5. customto yield crude product which
  6. customwas then triturated with hexanes
  7. customto give pure product as a white solid

Sources & evidence

ORD record
ord-28d15258a84b424d831ae9bc4f89c9cb
Source dataset
uspto-grants-2010_05
Patent number
US07723326B2

Reaction notes

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