Acetic Acid → HCID 21877809, compound

HRID 1991266Notes

Reaction equation

HRID 1991266 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[CH3:12][C:13]([CH3:15])=O.C([BH3-])#N.[Na+].CC(O)=O>CCO>[CH:13]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11])([CH3:15])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 180Acetone2×HCID 49847212-Amino-5-NitrophenolHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 21877809HCID 21877809, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-amino-5-nitrophenol (2.00 g, 13.0 mmol) in absolute EtOH (52 mL) and acetone (14.3 mL, 195 mmol, 15 equiv.) is treated with sodium cyanoborohydride (408 mg, 6.49 mmol), the pH is adjusted to 4.5-5.0 with glacial AcOH, and the mixture is stirred at ambient temperature for 4 days, during which time additional acetone (2×14.3 mL), sodium cyanoborohydride (3×408 mg) and glacial AcOH is added. The reaction mixture is then readjusted to pH 6, concentrated under reduced pressure, diluted with water (50 mL) and CH2Cl2 (75 mL), and the layers are separated. The organic phase is washed with saline (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue is chromatographed on a Flash 40M 90 g silica gel cartridge with EtOAc/heptane (20/80). Pooling and concentration of those fractions with an Rf=0.59 by TLC (EtOAc/hexanes, 50/50) gives the title compound, mp 108-110° C.; MS (ESI+) for C9H12N2O3 m/z 197 (M+H)+.

Workup

  1. additionis added
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water (50 mL) and CH2Cl2 (75 mL)
  4. customthe layers are separated
  5. washThe organic phase is washed with saline (25 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue is chromatographed on a Flash 40M 90 g silica gel cartridge with EtOAc/heptane (20/80)

Sources & evidence

ORD record
ord-32365ea7c8eb430bb0fe1aa232d0324d
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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