Sodium Dithionite → HCID 43345909, compound

HRID 2209119Notes

Reaction equation

HRID 2209119 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:12])[CH2:9][CH2:10][OH:11])=[C:4]([N:13]=O)[CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1>[NH2:13][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[N:8]([CH3:12])[CH2:9][CH2:10][OH:11]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 117844178HCID 117844178, compound

Product 1

HCID 43345909HCID 43345909, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-((4-bromo-2-nitrosophenyl)(methyl)amino)ethanol (6.5 g, 0.025 mol) was dissolved in THF (100 ml), Sodium hydrosulfite (26.2 g, 0.15 mol in water 150 mL) was added. The reaction was stirred at rt for 1 h. The mixture was extracted with EtOAc (2×100 ml). The combined organic layers was concentrated and purified by flash chromatography eluted with EtOAc to give 3.1 g, (50.3%) of 2-((2-amino-4-bromophenyl)(methyl)amino)ethanol LCMS-ESI+ (m/z): [M+H]+ calcd for C9H13BrN2O4:244.03; found 244.96, 246.91.

Workup

  1. extractionThe mixture was extracted with EtOAc (2×100 ml)
  2. concentrationThe combined organic layers was concentrated
  3. custompurified by flash chromatography
  4. washeluted with EtOAc

Sources & evidence

ORD record
ord-8c3dde06bfd44c8784b46ac7ce224e2e
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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