N-Methylaniline → 2,3-Dihydro-4-methyl-2-[2-(methylphenylamino)ethyl]pyrido[3,2-f][1,4]oxazepin-5(4H)-one

HRID 364415Notes

Reaction equation

HRID 364415 reaction equation
Cl.Cl[CH2:3][CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[O:6]1.[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:12][N:10]1[C:9](=[O:13])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[O:6][CH:5]([CH2:4][CH2:3][N:19]([CH3:18])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:11]1

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 137264372-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)one hydrochloride

Product 1

HCID 212714452,3-Dihydro-4-methyl-2-[2-(methylphenylamino)ethyl]pyrido[3,2-f][1,4]oxazepin-5(4H)-oneYield 31%

Conditions

Temperature
95 °C

Procedure

2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one hydrochloride, 4.00 g (0.015 mole) was dissolved in N-methylaniline (30 ml) and heated to 95° C. with stirring for 2 days. Excess N-methylaniline was removed by rotary evaporation (95° C., vacuum pump). The residue was taken up in chloroform (80 ml) and washed with dilute aqueous sodium hydroxide (30 ml) The chloroform layer was decolorized with activated carbon and dried over sodium sulfate, filtered and concentrated by rotary evaporation. The remaining residue was dissolved in ethyl acetate (50 ml) and purified by high pressure liquid chromatography using a silica gel column and ethyl acetate as the eluent. After purification, crystals formed from ethyl acetate. These crystals were recrystallized from ethyl acetate, giving 1.40 g (31%) of pale brown crystals.

Workup

  1. customExcess N-methylaniline was removed by rotary evaporation (95° C., vacuum pump)
  2. washwashed with dilute aqueous sodium hydroxide (30 ml) The chloroform layer
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. dissolutionThe remaining residue was dissolved in ethyl acetate (50 ml)
  7. custompurified by high pressure liquid chromatography
  8. customAfter purification, crystals
  9. customformed from ethyl acetate
  10. customThese crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fa9beb3c5b3847a1a7dd88135c59d9de
Source dataset
uspto-grants-1986_08
Patent number
US04604388

Reaction notes

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