Methanol → HCID 68281549, compound

HRID 1484534Notes

Reaction equation

HRID 1484534 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=O)[CH3:2].[CH3:10][OH:11].[OH-:12].[Na+]>[Pd]>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([C:4]2[CH:9]=[CH:8][C:10]([OH:11])=[CH:2][C:1]=2[OH:12])[CH3:2])[CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 95893-AcetylpyridineHCID 14798Sodium Hydroxide

Product 1

HCID 68281549HCID 68281549, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Pd/C (10%, 50% wet) (2 g; 50% by mass) is added to a solution of compound (16) (4 g; 70% by mass; 6.8 mmol, 1.0 eq) in a methanol/1 M aqueous HCl solution mixture (120 ml/40 ml). The suspension is stirred for 4 days under hydrogen atmosphere and then filtered using a Buchner funnel. The filtrate is evaporated under reduced pressure. The oil obtained is taken up in 1 M aqueous sodium hydroxide solution (160 ml) and washed with ethyl acetate (2×80 ml). The aqueous phase is neutralized by adding solid NaH2PO4 and then filtered using a Buchner funnel. The solid obtained is washed thoroughly with water and then dried under strong vacuum to lead to compound 3 (0.5 g; 35%) obtained as a beige solid.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated under reduced pressure
  3. customThe oil obtained
  4. washwashed with ethyl acetate (2×80 ml)
  5. additionby adding solid NaH2PO4
  6. filtrationfiltered
  7. customThe solid obtained
  8. washis washed thoroughly with water
  9. customdried under strong vacuum
  10. customobtained as a beige solid

Sources & evidence

ORD record
ord-013a5940d95441488e0b29d42511c0d5
Source dataset
uspto-grants-2016_08
Patent number
US09422261B2

Reaction notes

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