Ethanol → 2-(beta,gamma-Dihydroxypropyl)amino-4,5-methylenedioxy-1-nitrobenzene

HRID 1199871Notes

Reaction equation

HRID 1199871 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[CH2:7]1[O:15][C:14]2[C:9](=[CH:10][C:11]([N+]([O-])=O)=[C:12]([N+:16]([O-:18])=[O:17])[CH:13]=2)[O:8]1.C(N(CC)CC)C.C(O)C>C(O)(=O)C.O>[OH:6][CH:3]([CH2:4][OH:5])[CH2:2][NH:1][C:11]1[CH:10]=[C:9]2[O:8][CH2:7][O:15][C:14]2=[CH:13][C:12]=1[N+:16]([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 735613-Amino-1,2-propanediolHCID 6113255,6-Dinitro-1,3-benzodioxole

Product 1

HCID 137426742-(beta,gamma-Dihydroxypropyl)amino-4,5-methylenedioxy-1-nitrobenzene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

0.6 mol (56.3g) of 3-amino-1,2-propanediol is added dropwise to a mixture, brought to reflux, prepared by adding 0.3 mol (63.6 g) of 4,5-methylenedioxy-1,2-dinitrobenzene and 46 ml of triethylamine to 90 ml of 96° strength ethanol. The reaction mixture is heated for 3 hours under reflux. After dilution with 600 ml of icecold water and neutralization with acetic acid, the expected product is drained. After recrystallization from acetonitrile, it melts at 120°-121° C.

Workup

  1. temperatureto reflux
  2. customprepared
  3. temperatureThe reaction mixture is heated for 3 hours
  4. temperatureunder reflux

Sources & evidence

ORD record
ord-017569fe652c4fc98ab7e26dce2c2ae6
Source dataset
uspto-grants-1990_02
Patent number
US04904276

Reaction notes

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