Hydrochloric Acid → 8-nitro-3,4-dihydro-2H-1,5-benzodioxepin-7-amine

HRID 1903171Notes

Reaction equation

HRID 1903171 reaction equation
Cl.[NH:2]([C:6]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:9]2[O:10][CH2:11][CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1)C(C)=O>CO>[NH2:2][C:6]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:9]2[O:10][CH2:11][CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 4578373HCID 4578373, compound

Product 1

HCID 42520338-nitro-3,4-dihydro-2H-1,5-benzodioxepin-7-amineYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

400 ml of 4 N hydrochloric acid in methanol were added dropwise at reflux temperature to 22.4 g of 7-acetamino-8-nitro-3,4-dihydro-2H-1,5-benzodioxepine in 2000 ml of methanol, then the mixture was boiled overnight. After evaporation, the residue was taken up in methylene chloride, washed with 2 N soda and twice with water, dried over sodium sulfate and again evaporated. The crude product was recrystallized from alcohol. 17.1 g (92.0% of theory) of 7-amino-8-nitro-3,4-dihydro-1H-1,5-benzodioxepine of melting point 125°-126° C. were obtained.

Workup

  1. customAfter evaporation
  2. washwashed with 2 N soda and twice with water
  3. dry with materialdried over sodium sulfate
  4. customagain evaporated
  5. customThe crude product was recrystallized from alcohol

Sources & evidence

ORD record
ord-658df50370374521bdc6f7592654cfc2
Source dataset
uspto-grants-1984_03
Patent number
US04435406

Reaction notes

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