Potassium Carbonate → 4-(2-(Dimethylamino)ethyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1917130Notes

Reaction equation

HRID 1917130 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:12][C:11](=[O:13])[CH2:10][O:9][C:8]=2[CH:14]=1)([O-:3])=[O:2].Cl.Cl[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][N:12]1[C:11](=[O:13])[CH2:10][O:9][C:8]2[CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]1=2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 591440824-(2-(Dimethylamino)ethyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (0.5 g, 2.575 mmol), 2-chloro-N,N-dimethylethanamine hydrochloride (0.37 g, 2.575 mmol), and K2CO3 (1.06 g, 7.726 mmol) in dry DMF (5 mL) was stirred at 100° C. overnight (18 hours). The reaction was brought to room temperature, diluted with water (100 mL), and the product was extracted into ethyl acetate (2×25 mL). The combined ethyl acetate layers were washed with brine (20 mL) and then dried (Na2SO4). The solvent was evaporated, and the crude material was purified by column chromatography (3:97 (2M NH3 in MeOH):CH2Cl2) to obtain the title compound (0.52 g, 76%) as a yellow solid. 1H NMR (DMSO-d6) δ 2.17 (s, 6H), 2.42 (t, 2H, J=6.6 Hz), 4.07 (t, 2H, J=6.6 Hz), 4.79 (s, 2H), 7.45 (d, 1H, J=9.0 Hz), 7.80 (d, 1H, J=2.7 Hz), 7.96 (dd, 1H, J=2.4, 9.0 Hz); ESI-MS (m/z, %): 266 (MH+, 100), 221 (66).

Workup

  1. customwas brought to room temperature
  2. extractionthe product was extracted into ethyl acetate (2×25 mL)
  3. washThe combined ethyl acetate layers were washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe crude material was purified by column chromatography (3:97 (2M NH3 in MeOH):CH2Cl2)

Sources & evidence

ORD record
ord-d88ffc99ae92433d9b7bfcd64b0fe6e8
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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