Water → 4-(2-Dimethylaminoethyl)-6-nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 1740742Notes

Reaction equation

HRID 1740742 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[NH:9][C:8]=2[CH:14]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20]Cl.O>C1COCC1.C1(C)C=CC=CC=1>[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][N:9]1[C:8]2[CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:12][CH2:11][C:10]1=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 105158064-(2-Dimethylaminoethyl)-6-nitro-2H-1,4-benzoxazin-3(4H)-oneYield 79%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-nitro-2H-1,4-benzoxazin-3(4H)-one (J. Med. Chem. 1989, 32, 1627-1630) (1 g, 5.7 mmol) in dry THF (20 ml) at 0° C. under argon, was added NaH (0.16 g, 5.7 mmol, 80% dispersion in mineral oil). A solution of 2-dimethylaminoethyl chloride (2.3 g, 20.8 mmol) in dry toluene (15 ml) was added and the reaction mixture heated under reflux for 19 hr. After cooling, water was added dropwise until effervescence had ceased, then the mixture was separated and the aqueous further extracted with EtOAc. The organic layers were combined, dried (Na2SO4) and evaporated under reduced pressure to give a pale brown solid (1.08 g, 79%).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 19 hr
  3. temperatureAfter cooling
  4. customthe mixture was separated
  5. extractionthe aqueous further extracted with EtOAc
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8262d06091d043c5809275b80cda5d99
Source dataset
uspto-grants-1999_10
Patent number
US05972935

Reaction notes

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