Methylamine → 1-(2-Methylamino-3,5-dinitrophenyl)-2-propanol

HRID 4759

Reaction equation

HRID 4759 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N+:14]([O-:16])=[O:15])[C:7]2[O:11][CH:10]([CH3:12])[CH2:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].[CH3:17][NH2:18]>C(O)C>[CH3:17][NH:18][C:7]1[C:6]([N+:14]([O-:16])=[O:15])=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:8]=1[CH2:9][CH:10]([OH:11])[CH3:12]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 198363332-Methyl-5,7-dinitro-2,3-dihydro-1-benzofuran

Product 1

HCID 198363251-(2-Methylamino-3,5-dinitrophenyl)-2-propanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.056 Mole (12.5 g) of 2,3-dihydro-5,7-dinitro-2-methyl-benzofuran is suspended in 100 ml of a 33% strength solution of methylamine in ethanol. After 10 hours' stirring at room temperature in a sealed Erlenmeyer, the reaction mixture is brought for 30 minutes to the refluxing temperature of the alcohol. After the mixture is cooled, the expected product precipitates. It is drained, washed with alcohol and then recrystallized from 50 ml of 96° strength ethanol. After being dried, 0.047 mole (12 g) is obtained of a product which melts at 132° C.

Workup

  1. temperatureAfter the mixture is cooled
  2. customthe expected product precipitates
  3. washwashed with alcohol
  4. customrecrystallized from 50 ml of 96° strength ethanol
  5. customAfter being dried
  6. custom0.047 mole (12 g) is obtained of a product which melts at 132° C.

Sources & evidence

ORD record
ord-52be2b750bf64c28aee0f8bfed4840c7
Source dataset
uspto-grants-1988_02
Patent number
US04727192

Linked notes

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