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Water → Dimethyl 2,6-diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarboxylate

HRID 1937044
Notes
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Reaction equation

HRID 1937044 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH:18]([CH3:20])[CH3:19])[NH:11][C:10]([CH:21]([CH3:23])[CH3:22])=[C:9]2[C:24]([O:26][CH3:27])=[O:25])=[CH:4][CH:3]=1.O.N(OC)=O.[OH-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:24]([O:26][CH3:27])=[O:25])=[C:10]([CH:21]([CH3:22])[CH3:23])[N:11]=[C:12]([CH:18]([CH3:19])[CH3:20])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 12231Methyl nitriteHCID 14798Sodium HydroxideHCID 11199700DIMETHYL 1,4-DIHYDRO-2,6-DIISOPROPYL-4-(4-FLUOROPHENYL)-PYRIDINE-3,5-DICARBOXYLATE

Product 1

HCID 9969567Dimethyl 2,6-diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

In a 4 1 glass reactor, 750 g 4-(4-fluorophenyl)-2,6-diisopropyl-3,5-di(methoxy-carbonyl)-1,4-dihydropyridine were mixed with 2250 g water and 245 g of acetic acid. Thereafter 7 mols of methyl nitrite were introduced at 58 to 60° C. After cooling to 20° C. 363 g of 45% by weight strength aqueous sodium hydroxide were added to result in an increase of the pH up to 9. The resulting suspension was filtered and the product that has been filtered off was washed twice with in each case 800 ml of water and then dried at 50 to 60° C. under reduced pressure. 708 g of 4-(4-fluoropheny) -2,6-diisopropyl-3,5-di(methoxy-carbonyl)-pyridine were isolated, which corresponds to a yield of 95% of theory.

Workup

  1. customto result in
  2. temperaturean increase of the pH up to 9
  3. filtrationThe resulting suspension was filtered
  4. filtrationthe product that has been filtered off
  5. washwas washed twice with in each case 800 ml of water
  6. customdried at 50 to 60° C. under reduced pressure

Sources & evidence

ORD record
ord-2975d5805cb8435d963c554b3f4f54e5
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06392050B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes