Formic acid methanol → 3-(2-Cyanoethoxy)carbonyl-2,6-diethyl-1,4-dihydro-4-(4-nitrophenyl)pyridine-5-carboxylic acid

HRID 322170Notes

Reaction equation

HRID 322170 reaction equation
C([O:8][C:9]([C:11]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:15]([C:26]([O:28][CH2:29][CH2:30][C:31]#[N:32])=[O:27])=[C:14]([CH2:33][CH3:34])[NH:13][C:12]=1[CH2:35][CH3:36])=[O:10])C1C=CC=CC=1.C(O)=O.CO>C(Cl)(Cl)Cl.[Pd]>[C:31]([CH2:30][CH2:29][O:28][C:26]([C:15]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:11]([C:9]([OH:10])=[O:8])=[C:12]([CH2:35][CH3:36])[NH:13][C:14]=1[CH2:33][CH3:34])=[O:27])#[N:32]

Participants

5

Reactant 2

HCID 18963719Formic acid methanolHCID 230040763-Benzyloxycarbonyl-5-(2-cyanoethoxy)carbonyl-2,6-diethyl-1,4-dihydro-4-(4-nitrophenyl)pyridine

Product 1

HCID 230041663-(2-Cyanoethoxy)carbonyl-2,6-diethyl-1,4-dihydro-4-(4-nitrophenyl)pyridine-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6212ChloroformSolvent

Procedure

The solution of 3-benzyloxycarbonyl-5-(2-cyanoethoxy) carbonyl-2,6-diethyl-1,4-dihydro-4-(4-nitrophenyl)pyridine (6.30 g, 13.0 mmol) in 250 ml of 4.4% (w/w) formic acid/MeOH mixture was stirred with Pd/C (10%, 6.0 g) for 30 min., the reaction was quenched by addition of 100 ml of CHCl3. The mixture was filtered and concentration of filtrate give a yellow powder, which was dissolved in CHCl3, washed with water and 1N HCl. After filtration and removal of solvent, 3-(2-cyanoethoxy)carbonyl-2,6-diethyl-1,4-dihydro-4-(4-nitrophenyl)pyridine-5-carboxylic acid was obtained as a yellow powder (4.5 g, 87%).

Workup

  1. customthe reaction was quenched by addition of 100 ml of CHCl3
  2. filtrationThe mixture was filtered
  3. customconcentration of filtrate give a yellow powder, which
  4. washwashed with water and 1N HCl
  5. filtrationAfter filtration and removal of solvent

Sources & evidence

ORD record
ord-f308699e32134e3c8db6fa2e2189139a
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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