Ammonium formate → 2,3-Dihydro-1,4-benzodioxin-5-amine

HRID 365291Notes

Reaction equation

HRID 365291 reaction equation
C([O-])=O.[NH4+].[N+:5]([C:8]1[C:17]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)([O-])=O>[Pd].CO>[O:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([NH2:5])[C:17]=2[O:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 122313185-Nitro-2,3-dihydro-1,4-benzodioxine

Product 1

HCID 117883872,3-Dihydro-1,4-benzodioxin-5-amineYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (3.40 g, 0.054 mol) and 10% palladium on charcoal (1.44 g) were added to a stirred solution of the product of example 12 (2.45 g, 0.0135 mol) in methanol (15 ml). After the considerable effervescence had ceased, the mixture was filtered, evaporated in vacuo and triturated with acetonitrile. The residue was purified by chromatography (silica; ether) to give the product (1.51 g).

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated in vacuo
  3. customtriturated with acetonitrile
  4. customThe residue was purified by chromatography (silica; ether)

Sources & evidence

ORD record
ord-0021ff8aeaa44237870b7859b8961298
Source dataset
uspto-grants-2000_10
Patent number
US06127357

Reaction notes

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