Phenacyl bromide → HCID 90409179, compound

HRID 589017Notes

Reaction equation

HRID 589017 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][C:13]=1[OH:21].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CC#N>[N+:18]([C:17]1[C:12]2[N:11]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:2][O:21][C:13]=2[CH:14]=[CH:15][CH:16]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 90409179HCID 90409179, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 2-bromoacetophenone (3.9 g, 19 mmol) [Aldrich, cat. #115835] was added portion wise to a stirred suspension of 2-amino-3-nitrophenol (2.5 g, 16 mmol) [Aldrich, cat. #297003] and K2CO3 (3.4 g, 24 mmol) in MeCN (100 mL) at room temperature. The reaction was monitored by LC/MS. After stirring for 3 h the reaction was complete and then EtOAc added and solution filtered to remove the solids and the organic layer was washed with water, 1 N HCl, brine, dried over MgSO4, filtered and concentrated to give 5-nitro-3-phenyl-2H-1,4-benzoxazine as a dark oil (4.1 g, 100%). LCMS calc. for C14H11N2O3 (M+H)+: m/z=255.3. found: 255.1.

Workup

  1. filtrationsolution filtered
  2. customto remove the solids
  3. washthe organic layer was washed with water, 1 N HCl, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-adbf32ab41674f9ea859533c680dde1b
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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