Water → 4-(4-fluorophenyl)-2,6-diisopropyl-3,5-di(methoxy-carbonyl)-pyridine

HRID 1937044Notes

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

Participants

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

customto result in
temperaturean increase of the pH up to 9
filtrationThe resulting suspension was filtered
filtrationthe product that has been filtered off
washwas washed twice with in each case 800 ml of water
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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