(7-Nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol → (7-Amino-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

HRID 2102969Notes

Reaction equation

HRID 2102969 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH:10]([CH2:13][OH:14])[O:9][C:8]=2[CH:15]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH:10]([CH2:13][OH:14])[O:9][C:8]=2[CH:15]=1

Participants

4

Reactant 1

HCID 12736685(7-Nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

Product 1

HCID 22036433(7-Amino-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanolYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(7-nitro-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methanol (1.0 g, 4.7 mmol) was dissolved in methanol (30 ml) and palladium on activated carbon was added (0.10 g, 5% wt). The mixture was shaken on a parr shaker under H2(g) atmosphere (60 psi) for 24 hours. The mixture was filtered through Celite® and evaporated to give 722 mg of material as a white solid (86%), which was used as such for the next step. M/z=182 (m+1). Lc: 0.82 minutes.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customevaporated

Sources & evidence

ORD record
ord-08478585f6f741c39f4819d445610dfc
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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