Nitrogen → 1-Methyl-3-{N-[beta-(4-hydroxyphenyl)ethyl]}carbamoyl-1,4-dihydropyridine

HRID 260193Notes

Reaction equation

HRID 260193 reaction equation
[I-].[CH3:2][N+:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9](=[O:20])[NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:4]=1.C(=O)(O)[O-].[Na+].N#N.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH3:2][N:3]1[CH:8]=[CH:7][CH2:6][C:5]([C:9](=[O:20])[NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:4]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 134734281-Methyl-3-{N-[beta-(4-hydroxyphenyl)ethyl]}carbamoylpyridinium iodide

Product 1

HCID 147506161-Methyl-3-{N-[beta-(4-hydroxyphenyl)ethyl]}carbamoyl-1,4-dihydropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold solution of 1.15 g (3 mmol) of the product of Example 27 in 200 ml of deaerated water, 1.5 g (18 mmol) sodium bicarbonate were added. While the mixture was bubbled with N2 gas, 2.09 g (12 mmol) of sodium dithionite were gradually added to the mixture. The mixture was stirred under N2 for 1 hr and then extracted twice, each with 100 ml of ethyl acetate. The combined extract was washed with water, dried over anhydrous Na2SO4 and distilled on rotovap. Yield, 0.38 g (50%) of yellowish semisolid which reduced alcoholic AgNO3TS instantaneously. (PMR as expected.)

Workup

  1. additionwere gradually added to the mixture
  2. extractionextracted twice
  3. extractionThe combined extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. distillationdistilled on rotovap
  7. customYield

Sources & evidence

ORD record
ord-9c0d00efe18f4cb6b745fe1303d9bee6
Source dataset
uspto-grants-1996_06
Patent number
US05525727

Reaction notes

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