Hydrochloric Acid → 4-(4-Cyano-2-methoxyphenyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxylic acid

HRID 2170967Notes

Reaction equation

HRID 2170967 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[C:14]([CH3:22])[CH:15]=[N:16][C:17]=3[O:19][CH2:20][CH3:21])[NH:12][C:11]([CH3:23])=[C:10]2[C:24]([O:26]CCC#N)=[O:25])=[C:5]([O:31][CH3:32])[CH:4]=1)#[N:2].[OH-].[Na+].C(OCC)C.Cl>COCCOC.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[C:14]([CH3:22])[CH:15]=[N:16][C:17]=3[O:19][CH2:20][CH3:21])[NH:12][C:11]([CH3:23])=[C:10]2[C:24]([OH:26])=[O:25])=[C:5]([O:31][CH3:32])[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 686005972-Cyanoethyl 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxylate

Product 1

HCID 593496564-(4-Cyano-2-methoxyphenyl)-5-ethoxy-1,4-dihydro-2,8-dimethyl-1,6-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

1.75 g (4.05 mmol) of the compound from Example 29A are dissolved in 60 ml of 1,2-dimethoxyethane/water (2:1 v/v), 8.09 ml (8.09 mmol) of 1 N sodium hydroxide solution are added, and the mixture is stirred at room temperature for one hour. 30 ml of diethyl ether are then added to the mixture, and the aqueous phase is acidified with 6 N hydrochloric acid. The resulting precipitate is filtered off and washed with water and a little diethyl ether. Drying in a vacuum drying oven at 40° C. results in 1.47 g (96% of theory) of the title compound.

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with water
  3. customDrying in a vacuum
  4. customdrying oven at 40° C.

Sources & evidence

ORD record
ord-ecace524758c46d482d49a8b4082075f
Source dataset
uspto-grants-2015_06
Patent number
US09051316B2

Reaction notes

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