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

HRID 726541Notes

Reaction equation

HRID 726541 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>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

4

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 1

HCID 887MethanolSolvent

Procedure

Ammonium formate (3.40 g, 0.054 mol) and 10% passadium on charcoal (1.44 g) were added to a stirred solution of the product of Example 1 (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-26b613ff02444771819a18f5eb1da362
Source dataset
uspto-grants-1998_01
Patent number
US05710149

Reaction notes

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