Thionyl Chloride → Lercanidipine Impurity 5

HRID 1496686Notes

Reaction equation

HRID 1496686 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]([C:9]1[CH:10]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:11]([C:17](O)=[O:18])=[C:12]([CH3:16])[NH:13][C:14]=1[CH3:15])=[O:8]>ClCCl>[Cl:3][C:17]([C:11]1[CH:10]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:9]([C:7]([O:6][CH3:5])=[O:8])=[C:14]([CH3:15])[NH:13][C:12]=1[CH3:16])=[O:18]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester

Product 1

HCID 13317254Lercanidipine Impurity 5

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.4 g, 3.4 mmol) was slowly added to a solution of 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (1.0 g, 3 mmol) in dichloromethane dropwisely at −25° C. After the completion of the dropwise addition, the reaction was continued under cooling in an ice bath until the solution became clear. After the completion of reaction, the reaction solution was rotary evaporated to dryness to produce a crude product, which was directly used in the next step.

Workup

  1. additionAfter the completion of the dropwise addition
  2. temperatureunder cooling in an ice bath until the solution
  3. customAfter the completion of reaction
  4. customthe reaction solution was rotary evaporated to dryness

Sources & evidence

ORD record
ord-75a3f88a3f84454ab1debf234b43bce9
Source dataset
uspto-grants-2015_12
Patent number
US09198902B2

Reaction notes

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