Nitric Acid → HCID 19042736, compound

HRID 1683153Notes

Reaction equation

HRID 1683153 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:22])=[C:5]([CH2:18][C:19]([OH:21])=[O:20])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[CH2:8][C:9]([OH:11])=[O:10].[N+]([O-])(O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:22][C:4]1[C:5]([CH2:18][C:19]([OH:21])=[O:20])=[C:6]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:7]([CH2:8][C:9]([OH:11])=[O:10])=[C:2]([CH3:1])[N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 11430Potassium CarbonateHCID 19042739HCID 19042739, compound

Product 1

HCID 19042736HCID 19042736, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

90.3 g (0.3 mol) of 1,4-dihydro-2,6-dimethyl-4-phenyl-3,5-bis(carboxymethyl)pyridine were added in portions at from 92° to 98° C. to a solution of 375 g of 98% strength nitric acid in 1580 ml of water in the course of 30 minutes. After a further 30 minutes at 95°-98° C., the mixture was cooled to +5° C. and brought to pH 9 with solid potassium carbonate. The mixture was extracted three times with methylene chloride, the combined extracts were concentrated under reduced pressure and the residue was crystallized at 0° C. using 1:1 diethyl ether/pentane (50 ml). 58.8 g (65.5% of theory) of 2,6-dimethyl-4-phenyl-3,5-bis(carboxymethyl)pyridine were obtained as white crystals of m.p. 137°-138° C.

Workup

  1. temperaturethe mixture was cooled to +5° C.
  2. extractionThe mixture was extracted three times with methylene chloride
  3. concentrationthe combined extracts were concentrated under reduced pressure
  4. customthe residue was crystallized at 0° C.

Sources & evidence

ORD record
ord-fadb2bc25f13406b9d416e649762f4d2
Source dataset
uspto-grants-1997_06
Patent number
US05637554

Reaction notes

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