Glycerol → 2,3-Dihydro4-(2-dimethylaminoethyl)-4H-pyrido[2,3-g][1,4]benzoxazine

HRID 1740744Notes

Reaction equation

HRID 1740744 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[C:6]=2[CH:16]=1.O[CH2:18][CH:19]([CH2:21]O)O.II.OS(O)(=O)=O.[OH-].[Na+]>O>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][N:7]1[C:6]2[CH:16]=[C:2]3[N:1]=[CH:21][CH:19]=[CH:18][C:3]3=[CH:4][C:5]=2[O:10][CH2:9][CH2:8]1

Participants

7

Reactant 5

HCID 753GlycerolHCID 807IodineHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 106805166-Amino-3,4-dihydro-4-(2-dimethylaminoethyl)-2H-1,4-benzoxazine

Product 1

HCID 218330252,3-Dihydro4-(2-dimethylaminoethyl)-4H-pyrido[2,3-g][1,4]benzoxazineYield 9.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

6-Amino-3,4-dihydro-4-(2-dimethylaminoethyl)-2H-1,4-benzoxazine (D3, 4.66 g, 21 mmol), glycerol (2.9 g, 31 mmol) and iodine (0.135 g, 0.5 mmol) were stirred as conc. H2SO4 (3.2 ml, 60 mmol) was cautiously added. The mixture was stirred at 180° C. for 2 h, cooled, dispersed in water (300 ml), basified (40% NaOH), and extracted with dichloromethane. The extract was dried (Na2SO4) and evaporated to an oil, which was chromatographed on silica, eluting with 20% methanol/dichloromethane. This gave the title compound (0.50 g, 9%) as a dark oil.

Workup

  1. additionwas cautiously added
  2. temperaturecooled
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract was dried (Na2SO4)
  5. customevaporated to an oil, which
  6. customwas chromatographed on silica
  7. washeluting with 20% methanol/dichloromethane

Sources & evidence

ORD record
ord-f33f678df8c14713bb13d1ed5a6acfa1
Source dataset
uspto-grants-1999_10
Patent number
US05972935

Reaction notes

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