Potassium Carbonate → 8-acetyl-5-benzyloxy-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

HRID 969452Notes

Reaction equation

HRID 969452 reaction equation
Br[C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[C:10]([OH:26])=[C:11]([C:23](=[O:25])[CH3:24])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:23]([C:11]1[C:10]2[O:26][C:2]([CH3:7])([CH3:6])[C:3](=[O:4])[NH:8][C:9]=2[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111060492-Bromo-2-methylpropanoyl chlorideHCID 579892521-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

Product 1

HCID 694623038-acetyl-5-benzyloxy-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

28 g (0.15 mol) 2-bromo-2-methyl-propionyl chloride are added dropwise to 25.7 g (0.10 mol) 1-(3-amino-4-benzyloxy-2-hydroxy-phenyl)-ethanone and 41 g (0.30 mol) potassium carbonate in 215 mL acetonitrile. After 8 hours stirring at reflux temperature the solid is filtered off, the filtrate is evaporated down and the residue is crystallised from ethanol. Yield: 11.2 g (35%); melting range=124-126° C.

Workup

  1. temperatureat reflux temperature the solid
  2. filtrationis filtered off
  3. customthe filtrate is evaporated down
  4. customthe residue is crystallised from ethanol

Sources & evidence

ORD record
ord-f0337e8baf2d425fbcfb556fbf7b4812
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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