Pyridoxal hydrochloride → HCID 136163973, compound

HRID 1487430Notes

Reaction equation

HRID 1487430 reaction equation
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+:21].[CH3:22][C:23]1[C:28]([OH:29])=[C:27]([CH:30]=O)[C:26]([CH2:32][OH:33])=[CH:25][N:24]=1.Cl.[OH-].[NH4+:36]>CS(C)=O>[C:1]1([C:7]2[N:21]=[C:30]([C:27]3[C:26]([CH2:32][OH:33])=[CH:25][N:24]=[C:23]([CH3:22])[C:28]=3[OH:29])[NH:36][C:9]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6171Pyridoxal hydrochlorideHCID 8651BenzilHCID 14923Ammonium HydroxideHCID 517165Ammonium Acetate

Product 1

HCID 136163973HCID 136163973, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
100 °C

Procedure

Benzil (2.10 g, 10 mmol), ammonium acetate (11.5 g, 150 mmol) were dissolved in DMSO (60 mL) and heated to 100° C. Pyridoxal hydrochloride (4.1 g, 20 mmol) in DMSO (50 mL) was added drop wise and after 100 min stirring at 100° C. the reaction mixture was 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. filtrationThe precipitate was filtered off
  2. washwashed with water (100 mL)
  3. dissolutiondissolved in ethyl acetate (150 mL)
  4. extractionextracted with water (2×50 mL)
  5. dry with materialThe organic layer was dried over MgSO4 (10 g)
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on silica gel eluting with toluene/acetone 7/3
  8. additionFractions containing product
  9. customwere evaporated to a volume of 50 mL
  10. temperaturecooled to 0° C
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-4fe504bada9d4fe384d53a4d78189f7a
Source dataset
uspto-grants-2016_08
Patent number
US09428533B2

Reaction notes

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