Hydrochloric Acid → HCID 135833463, compound

HRID 247121Notes

Reaction equation

HRID 247121 reaction equation
C[O:2][CH:3](OC)[C:4]1[NH:9][C:8]([CH3:10])=[C:7]([C:11]2[O:15][N:14]=[C:13]([CH2:16][N:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:18])[N:12]=2)[CH:6]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=2)[C:5]=1[C:35]([O:37][CH3:38])=[O:36].Cl.C(=O)(O)[O-].[Na+]>CC(C)=O>[CH2:19]([N:17]([CH2:16][C:13]1[N:12]=[C:11]([C:7]2[CH:6]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=3)[C:5]([C:35]([O:37][CH3:38])=[O:36])=[C:4]([CH:3]=[O:2])[NH:9][C:8]=2[CH3:10])[O:15][N:14]=1)[CH3:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 135833462HCID 135833462, compound

Product 1

HCID 135833463HCID 135833463, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.0 g of methyl 1,4-dihydro-6-dimethoxymethyl-3-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-2-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate in 15 ml of acetone was added 2 ml of 6N-hydrochloric acid. After stirring at room temperature for 3 hours, the reaction mixture was neutralized with sodium bicarbonate solution and then concentrated in vacuo. To the residue was added ethyl acetate and the resultant solution was washed with water, dried and evaporated in vacuo. The residue was chromatographed on silica gel using chloroform-methanol (50:1) as eluent to give 740 mg of methyl 1,4-dihydro-3-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-6-formyl-2-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate, IR νmaxneat cm-1 : 3350, 1700, 1680, 1640, 1600, 1520.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the residue was added ethyl acetate
  3. washthe resultant solution was washed with water
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-8b449d44558041ce8483c9474d2d0cea
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Reaction notes

Loading…