Water → HCID 10490884, compound

HRID 1635043Notes

Reaction equation

HRID 1635043 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:13](=[O:14])[NH:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[O:9]2)[CH:5]=[CH:6][CH:7]=1.O.[CH3:20][N:21](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:20]([C:2]1[CH:3]=[C:4]([CH:8]2[C:13](=[O:14])[NH:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[O:9]2)[CH:5]=[CH:6][CH:7]=1)#[N:21]

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 10685900HCID 10685900, compound

Product 1

HCID 10490884HCID 10490884, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(3-bromophenyl)-3,4-dihydro-2H-1,4-benzoxazin-3-one (I7) (3.00 g, 9.87 mmol) in DMF (20 mL) was added Zinc cyanide (0.68 g, 5.79 mmol) and then tetrakistriphenylphosphine palladium (0) (0.96 g, 8 mol %). The degassed solution was heated at 100° C. for 5 hours, cooled to room temperature, and then treated with water (50 mL). The product was extracted into ethyl acetate (2×100 mL), washed with brine (50 mL), dried over MgSO4, and then purified by silica gel chromatography, eluant 50% ethyl acetate in hexane. This process affords the title compound (1.866 g, 76%) that was recrystallized from ethanol/water.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe product was extracted into ethyl acetate (2×100 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. custompurified by silica gel chromatography, eluant 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3fe6a44b8afd4f9a8c6432389adb3b7d
Source dataset
uspto-grants-2003_01
Patent number
US06509335B1

Reaction notes

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