Hydrochloric Acid → 6-amino-3,4-epoxy-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1-benzopyran

HRID 1108219Notes

Reaction equation

HRID 1108219 reaction equation
O1CCOCC1.C([NH:10][C:11]1[C:12]([N+:24]([O-:26])=[O:25])=[CH:13][C:14]2[O:19][C:18]([CH3:21])([CH3:20])[CH:17]3[O:22][CH:16]3[C:15]=2[CH:23]=1)(=O)C.[OH-].[Na+].Cl>O>[NH2:10][C:11]1[C:12]([N+:24]([O-:26])=[O:25])=[CH:13][C:14]2[O:19][C:18]([CH3:21])([CH3:20])[CH:17]3[O:22][CH:16]3[C:15]=2[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 110657616-Acetamido-3,4-epoxy-3,4-dihydro-2,2-dimethyl-7-nitro-2H-benzo[b]pyran

Product 1

HCID 146739026-amino-3,4-epoxy-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1-benzopyranYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixed solution of a 1,4-dioxane (152 mL) and water (76 mL) in which a 6-acetoamido-3,4-epoxy-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1-benzopyran (synthesized according to the method of Evans, J. M., et al., J. Med. Chem. 1984, 27, 1127) (7.6 g, 27 mmol) and sodium hydroxide (5.6 g, 5.0 eq.) were dissolved was stirred at room temperature for four hours. After the mixture was neutoralized with hydrochloric acid, the resulting product was diluted by a saturated saline water, extracted with an ethyl acetate and then, dried over a sodium sulfate anhydride. After the solvent was distilled off, the resulting product was recrystallized from a mixed solvent of ethanol and hexane to obtain a 6-amino-3,4-epoxy-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1-benzopyran (1.4 g, 22%) as orange crystals.

Workup

  1. extractionextracted with an ethyl acetate
  2. dry with materialdried over a sodium sulfate anhydride
  3. distillationAfter the solvent was distilled off
  4. customthe resulting product was recrystallized from a mixed solvent of ethanol and hexane

Sources & evidence

ORD record
ord-b813d420eec0417e9b74c246848c6400
Source dataset
uspto-grants-2000_05
Patent number
US06066631

Reaction notes

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