Triethylamine → Benzo[1,3]dioxol-5-ylmethyl-(4-chloro-7-nitro-phthalazin-1-yl)-amine

HRID 863204Notes

Reaction equation

HRID 863204 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[C:5](Cl)=[N:4][N:3]=1.[CH2:16]([NH2:26])[C:17]1[CH:25]=[CH:24][C:23]2[O:22][CH2:21][O:20][C:19]=2[CH:18]=1.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([NH:26][CH2:16][C:17]2[CH:25]=[CH:24][C:23]3[O:22][CH2:21][O:20][C:19]=3[CH:18]=2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 108003021,4-Dichloro-6-nitrophthalazine

Product 1

HCID 10546352Benzo[1,3]dioxol-5-ylmethyl-(4-chloro-7-nitro-phthalazin-1-yl)-amineYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.5 g of the 1,4-dichloro-6-nitrophthalazine prepared in the step (a) was dissolved in 100 ml of ethanol, followed by the addition thereto of 2.17 g of piperonylamine and 3 ml of triethylamine. The resultant mixture was heated under reflux for 12 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. Water was added to the residue thus obtained to give a solution. The obtained aqueous solution was extracted with methylene chloride. The organic phase was dried over magnesium sulfate and then subjected to vacuum concentration to remove the solvent. The residue was purified by silica gel column chromatography [n-hexane/ethyl acetate (2: 1 to 1: 1)]. Thus, 1.8 g of 1-chloro-4-(3,4-methylenedioxybenzyl)amino-6-nitrophthalazine was obtained from less polar fractions as a yellow solid and 1.2 g of 1-chloro-4-(3,4-methylene-dioxybenzyl)amino-7-nitrophthalazine was obtained from more polar fractions as a yellow solid.

Workup

  1. additionfollowed by the addition
  2. temperatureunder reflux for 12 hours
  3. distillationThe reaction mixture was distilled under reduced pressure
  4. customto remove the solvent
  5. additionWater was added to the residue
  6. customthus obtained
  7. customto give a solution
  8. extractionThe obtained aqueous solution was extracted with methylene chloride
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. concentrationsubjected to vacuum concentration
  11. customto remove the solvent
  12. customThe residue was purified by silica gel column chromatography [n-hexane/ethyl acetate (2: 1 to 1: 1)]

Sources & evidence

ORD record
ord-8620fc674d504164b9cd6f37058244d4
Source dataset
uspto-grants-1998_02
Patent number
US05719303

Reaction notes

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