Acetic Acid → HCID 25219450, compound

HRID 425191Notes

Reaction equation

HRID 425191 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[O:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.C(O)(=O)C.C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:12]2[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 97314-FluoroanilineHCID 14798Sodium HydroxideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 25219450HCID 25219450, compoundYield 739.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-fluoroaniline (1 g; 0.9 mmol) and tetrahydro-4H-pyran-4-one (0.98 g; 1.1 equiv.) in methanol (20 ml) was treated with acetic acid (0.67 ml; 1.3 equiv.) and sodium cyanoborohydride (0.73 g; 1.3 equiv.) then stirred at room temperature overnight. The reaction was cooled to 0° C., basified with 2M sodium hydroxide solution and the resultant solid collected by filtration, washed with water and dried under vacuum to give 1.3 g of the title compound. 1H NMR (DMSO-d6) 6.80 (2H, t), 6.48 (2H, dd), 5.25 (1H, d), 3.75 (2H, dt), 3.33-3.23 (3H, m), 1.78-1.71 (2H, m), 1.28-1.18 (2H, m).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. filtrationthe resultant solid collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4c1921386cac4a83b6de6e8f2fabd635
Source dataset
uspto-grants-2012_01
Patent number
US08106057B2

Reaction notes

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