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

HRID 970645Notes

Reaction equation

HRID 970645 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 a 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 through a filter paper
  2. concentrationthe filtrate concentrated under vacuum to a white solid
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to a white solid
  5. customused for the next reaction without further purification

Sources & evidence

ORD record
ord-ea311c1534364d8dac9c50afd68a5813
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Reaction notes

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