Sodium Nitrite → HCID 57567341, compound

HRID 1915345Notes

Reaction equation

HRID 1915345 reaction equation
N[C:2]1[CH:3]=[C:4]([NH:17][C:18](=[O:20])[CH3:19])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:16])([CH3:15])[CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14].N([O-])=[O:22].[Na+]>OS(O)(=O)=O>[OH:22][C:2]1[CH:3]=[C:4]([NH:17][C:18](=[O:20])[CH3:19])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:16])([CH3:15])[CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 57567410HCID 57567410, compound

Product 1

HCID 57567341HCID 57567341, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of N-{3-amino-4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenyl}-acetamide (1.6 g, 5.7 mmol) in H2SO4 (15%, 6 mL) was added NaNO2 at 0-5° C. The mixture was stirred at this temperature for 20 min and then poured into ice water. The mixture was extracted with EtOAc (30 mL×3). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (petroleum ether-EtOAc, 100:1) to give N-{3-hydroxy-4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenyl}-acetamide (0.7 g, 38%).

Workup

  1. extractionThe mixture was extracted with EtOAc (30 mL×3)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (petroleum ether-EtOAc, 100:1)

Sources & evidence

ORD record
ord-ff2baecb3a344dca84edecaf88a823f4
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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