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

HRID 1583800Notes

Reaction equation

HRID 1583800 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 4N 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 2N 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 2N 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-82670ba066a94cddbafa9896315797c6
Source dataset
uspto-grants-1985_11
Patent number
US04554280

Reaction notes

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