Ammonia → 1-(2-Amino-3,5-dinitrophenyl)-2-propanol

HRID 4758

Reaction equation

HRID 4758 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].[NH3:17].COCCO>O>[NH2:17][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

5

Reactant 3

HCID 222AmmoniaHCID 80192-MethoxyethanolHCID 198363332-Methyl-5,7-dinitro-2,3-dihydro-1-benzofuran

Product 1

HCID 198363271-(2-Amino-3,5-dinitrophenyl)-2-propanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

0.39 Mole (88 g) of 2,3-dihydro-5,7-dinitro-2-methylbenzofuran, prepared according to J.A.C.S. 80, p. 4711-4714 (1958), is suspended in 1.1 l of 20% strength ammonia solution and 600 ml of Methyl Cellosolve. After 18 hours' heating at 70° C., the reaction mixture is cooled. The precipitate formed is drained and, after being made into a paste in water until neutral and then dried under vacuum, is recrystallized from 170 ml of dioxane. After being dried under vacuum, 0.30 mole (72 g) of the expected product is obtained; it melts at 177° C.

Workup

  1. temperaturethe reaction mixture is cooled
  2. customThe precipitate formed
  3. customthen dried under vacuum
  4. customis recrystallized from 170 ml of dioxane
  5. customAfter being dried under vacuum

Sources & evidence

ORD record
ord-5155b74041e040c5848aa97537ebe3cb
Source dataset
uspto-grants-1988_02
Patent number
US04727192

Linked notes

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