Pyridoxal hydrochloride → HCID 136163971, compound

HRID 1487431Notes

Reaction equation

HRID 1487431 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=O)=O)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:23].[CH3:24][C:25]1[C:30]([OH:31])=[C:29]([CH:32]=O)[C:28]([CH2:34][OH:35])=[CH:27][N:26]=1.Cl.[OH-].[NH4+:38]>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:23]=[C:32]([C:29]3[C:28]([CH2:34][OH:35])=[CH:27][N:26]=[C:25]([CH3:24])[C:30]=3[OH:31])[NH:38][C:10]=2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6171Pyridoxal hydrochlorideHCID 14923Ammonium HydroxideHCID 1230724,4'-DifluorobenzilHCID 517165Ammonium Acetate

Product 1

HCID 136163971HCID 136163971, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
100 °C

Procedure

4,4′-Difluorobenzil (2.46 g, 10 mmol), ammonium acetate (11.5 g, 150 mmol) were dissolved in DMSO (60 mL) and heated to 100° C. Pyridoxal hydrochloride (6.1 g, 30 mmol) in DMSO (50 mL) was added drop wise over a period of 40 min. The reaction mixture was cooled to it and poured into icewater (300 mL) and aq. ammonium hydroxide solution (50 mL). The precipitate was filtered off, washed with water (100 mL), dissolved in ethyl acetate (150 mL) and extracted with water (2×50 mL). The organic layer was dried over MgSO4 (10 g) and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with toluene/acetone 7/3. Fractions containing product were evaporated to a volume of 50 mL and cooled to 0° C. The precipitate was filtered off and dried to give (250 mg) the title compound as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to it
  2. filtrationThe precipitate was filtered off
  3. washwashed with water (100 mL)
  4. dissolutiondissolved in ethyl acetate (150 mL)
  5. extractionextracted with water (2×50 mL)
  6. dry with materialThe organic layer was dried over MgSO4 (10 g)
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography on silica gel eluting with toluene/acetone 7/3
  9. additionFractions containing product
  10. customwere evaporated to a volume of 50 mL
  11. temperaturecooled to 0° C
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-697c3d0d51bf4a5ea203fd5af45c20bf
Source dataset
uspto-grants-2016_08
Patent number
US09428533B2

Reaction notes

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