Acetic Acid → HCID 481016, compound

HRID 1840725Notes

Reaction equation

HRID 1840725 reaction equation
N[C:2]1[C:3](=[O:20])[NH:4][C:5]([CH3:19])=[C:6]([CH2:17][CH3:18])[C:7]=1[CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=1.C=O.[C:23]([BH3-])#[N:24].[Na+].[C:27](O)(=O)C>C(#N)C>[CH3:27][N:24]([CH3:23])[C:2]1[C:3](=[O:20])[NH:4][C:5]([CH3:19])=[C:6]([CH2:17][CH3:18])[C:7]=1[CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 712FormaldehydeHCID 481003HCID 481003, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 481016HCID 481016, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-amino-4-(3,5-dimethylbenzyl)-5-ethyl-6-methylpyridin-2(1H)-one (200 mg) and 37% of aqueous formaldehyde (0.60 mL) in 5 mL of acetonitrile was added 139 mg of sodium cyanoborohydride. Glacial acetic acid (0.07 mL) was added dropwise and the reaction mixture was stirred at room temperature for 2 hours. An additional 0.07 mL of glacial acetic acid was added, and stirring was continued for 30 minutes. The solvent was evaporated and 15 mL ether were added to the resulting residue. The organic layer was washed with 3×30 mL 1N aqueous potassium hydroxide and 3 mL brine, dried over magnesium sulfate and concentrated under reduced pressure to give 3-dimethylamino4-(3,5-dimethylbenzyl)-5-ethyl-6-methylpyridin-2(1H)-one (200 mg, 91%) mp 229-230° C.

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes
  3. customThe solvent was evaporated
  4. addition15 mL ether were added to the resulting residue
  5. washThe organic layer was washed with 3×30 mL 1N aqueous potassium hydroxide and 3 mL brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-010b6771f3e5463180561a79b299366b
Source dataset
uspto-grants-2004_01
Patent number
US06683079B2

Reaction notes

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