Acetic Acid → HCID 21999476, compound

HRID 1976938Notes

Reaction equation

HRID 1976938 reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[CH:10][C:11]=1[F:12].C=O.[C:16](O)(=O)C>C(#N)C.O>[CH3:16][N:2]([CH3:1])[C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[CH:10][C:11]=1[F:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 135191803-Amino-4-fluorophenol

Product 1

HCID 21999476HCID 21999476, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Sodium cyanoborohydride (0.81 g, 12.7 mmol) is added to a solution of 3-amino-4-fluorophenol (0.66 g, 4.6 mmol), formaldehyde (37% solution, 2.0 g, 24.6 mmol) and acetic acid (0.5 mL) in 20 mL acetonitrile. The reaction is stirred for 2 hour and then poured into 100 mL water. The product is then extracted into diethyl ether (50 mL×3) and the combined organic fractions are washed with brine (40 mL), and dried over anhydrous sodium sulfate. The resulting solution is concentrated in vacuo, and the residue is chromatographed on silica gel using CHCl3:ethyl acetate as eluant (99:1 to 90:10 gradient) to yield 0.72 g (91%) of Compound 22 as a brown solid. 1H-NMR (CDCl3) 6.85 (dd, 1H); 6.40 (m, 1H); 6.27 (m, 1H); 2.84 (s, 6H). 1H-NMR (CDCl3) 133.25 (t, J=9.5 Hz).

Workup

  1. extractionThe product is then extracted into diethyl ether (50 mL×3)
  2. washthe combined organic fractions are washed with brine (40 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe resulting solution is concentrated in vacuo
  5. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-26b5bb997239418d96370994ef1d09ae
Source dataset
uspto-grants-2001_05
Patent number
US06229055B1

Reaction notes

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