6-amino-4-methyl-2H-1,4-benzoxazin-3(4H)-one → HCID 59377423, compound

HRID 386662Notes

Reaction equation

HRID 386662 reaction equation
[Br-:1].C([N+](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C)(C)C.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]2[O:28][CH2:27][C:26](=[O:29])[N:25]([CH3:30])[C:24]=2[CH:31]=1>C(Cl)Cl.CO>[NH2:19][C:20]1[C:21]([Br:1])=[CH:22][C:23]2[O:28][CH2:27][C:26](=[O:29])[N:25]([CH3:30])[C:24]=2[CH:31]=1

Participants

5

Reactant 2

HCID 27644636-amino-4-methyl-2H-1,4-benzoxazin-3(4H)-oneHCID 98185972-Propanaminium, N,N,N-tris(1,1-dimethylethyl)-2-methyl-, bromide

Product 1

HCID 59377423HCID 59377423, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Tetra-tert-butyl ammonium bromide (6.77 g, 14.04 mmol) was added to a solution of 6-amino-4-methyl-4H-benzo[1,4]oxazin-3-one (2.5 g, 14.04 mmol) in methylene chloride (100 ml) and MeOH (50 ml). The mixture was stirred at room temperature for 20 minutes, then quenched with aqueous sodium bisulfite solution. The mixture was extracted with methylene chloride, and the combined organic extracts were dried over MgSO4, filtered, concentrated under reduced pressure and purified via column chromatography to give 1.30 g of 6-amino-7-bromo-4-methyl-4H-benzo[1,4]oxazin-3-one as a light yellow solid, 40%.

Workup

  1. customquenched with aqueous sodium bisulfite solution
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-542b3f87ce0840ea9a032193ac67d623
Source dataset
uspto-grants-2013_02
Patent number
US08372865B2

Reaction notes

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