Methanol → HCID 14989569, compound

HRID 1111117Notes

Reaction equation

HRID 1111117 reaction equation
[CH3:1][O-:2].[Na+].Cl.[NH2:5][C:6]1([C:12]2[CH:13]=[CH:14][C:15](=[O:18])[NH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:19]O>>[O:18]=[C:15]1[NH:16][CH:17]=[C:12]([C:6]2([NH:5][C:1](=[O:2])[CH3:19])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH:13]=[CH:14]1

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 19768457HCID 19768457, compound

Product 1

HCID 14989569HCID 14989569, compound

Procedure

Sodium methoxide solution (25% in methanol, 6 ml) was added to a suspension of 5-(1-aminocyclohexyl)-2(1H)-pyridinone hydrochloride (6.0 g) in 100 ml of methanol, and the mixture was stirred at room temperature for 10 minutes. The solvent was removed in vacuo, and the residual solids were suspended in 260 ml of dichloromethane. Poly-4-vinylpyridine (5.42 g), acetic anhydride (2.67 g) and a catalytic amount of 4-(N,N-dimethylamino)pyridine were added, and the mixture was stirred at room temperature for 2 hours. The suspension was filtered and the solid residue was washed with methanol. The filtrate was concentrated, leaving 4.9 g of solid. Recrystallization from methanol gave 1.69 g of product (m.p. 238°-242° C. dec) in two crops, each of which was analytically pure.

Workup

  1. customThe solvent was removed in vacuo
  2. additionPoly-4-vinylpyridine (5.42 g), acetic anhydride (2.67 g) and a catalytic amount of 4-(N,N-dimethylamino)pyridine were added
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. filtrationThe suspension was filtered
  5. washthe solid residue was washed with methanol
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ffbb35daa29244e4ad903038839e91cc
Source dataset
uspto-grants-1990_12
Patent number
US04978663

Reaction notes

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