(6-Nitro-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol → (6-Amino-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

HRID 2102971Notes

Reaction equation

HRID 2102971 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[O:8][CH:9]([CH2:12][OH:13])[CH2:10][O:11][C:6]=2[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]2[O:8][CH:9]([CH2:12][OH:13])[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 12736691(6-Nitro-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

Product 1

HCID 21988145(6-Amino-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanolYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(6-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 646 mg of material as a white solid (77%), 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-26a5249b4a3e46cc8144b916a06b5d77
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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