Ammonium Hydroxide → 2-((Cyclopropylmethoxy)methyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-amine

HRID 2102943Notes

Reaction equation

HRID 2102943 reaction equation
[CH:1]1([CH2:4][O:5][CH2:6][CH:7]2[O:12][C:11]3[CH:13]=[CH:14][C:15]([N+:17]([O-])=O)=[CH:16][C:10]=3[O:9][CH2:8]2)[CH2:3][CH2:2]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH4+].[OH-]>O1CCOCC1.O>[CH:1]1([CH2:4][O:5][CH2:6][CH:7]2[O:12][C:11]3[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:10]=3[O:9][CH2:8]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 687021632-((Cyclopropylmethoxy)methyl)-2,3-dihydro-6-nitrobenzo[b][1,4]dioxine

Product 1

HCID 590206732-((Cyclopropylmethoxy)methyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

2-((Cyclopropylmethoxy)methyl)-2,3-dihydro-6-nitrobenzo[b][1,4]dioxine (0.33 g, 0.0012 mol) was dissolved in 20 mL dioxane. Sodium dithionite (2.2 g, 0.013 mol) was suspended in water (4 mL) and NH4OH (2 mL) and then added to the dioxane solution. The reaction was stirred at room temp for 6 hrs. The mixture was filtered through filter paper and the filtrate concentrated under vacuum to a white solid. The solid was suspended in 10% EtOAc/hexanes and filtered. The filtrate was concentrated to a white solid and used for the next reaction without further purification. Yield of the title compound is 0.29 g (98%). m/z=235.8 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthrough filter paper
  3. concentrationthe filtrate concentrated under vacuum to a white solid
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated to a white solid
  6. customused for the next reaction without further purification

Sources & evidence

ORD record
ord-da1d7bdda921463dadfab30b47f5c4bc
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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