Acetic Acid → HCID 22117948, compound

HRID 1275937Notes

Reaction equation

HRID 1275937 reaction equation
C([BH3-])#N.[Na+].[NH2:5][C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[CH:10][C:11]=1[F:12].[CH2:14]=[O:15].[C:16]([OH:19])(=O)C>C(#N)C.O>[CH3:14][O:15][N:5]([O:19][CH3:16])[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 22117948HCID 22117948, 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). 19F-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-05b22716e698454c8f3a4be2ebcd6861
Source dataset
uspto-grants-2000_12
Patent number
US06162931

Reaction notes

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