Hydrogen Bromide → HCID 19980425, compound

HRID 1461403Notes

Reaction equation

HRID 1461403 reaction equation
[BrH:1].[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[C:11]2[NH:12][C:13]([CH3:33])=[C:14]([C:31]#[N:32])[CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=3)[C:16]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C(O)(=O)C.C(Cl)(Cl)Cl>[C:2]1([CH:8]([Br:1])[CH2:10][CH2:9][C:11]2[NH:12][C:13]([CH3:33])=[C:14]([C:31]#[N:32])[CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=3)[C:16]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 22841808HCID 22841808, compound

Product 1

HCID 19980425HCID 19980425, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

5 ml of a solution of hydrobromic acid in 30% acetic acid are added at 25° C. and under inert atmosphere to a solution of the less polar diastereoisomer of trans-2-(2-phenyl-1-cyclopropyl)-3-carboethoxy-5-cyano-6-methyl-4-(m-nitrophenyl)-1,4-dihydropyridine (0.5 g) in chloroform (5 ml). After 1 1/5 hours the mixture is poured into water (50 ml) and extracted with diethyl ether (25 ml). The phases are separated and the organic one is washed with a 5% NaHCO3 aqueous solution (3×50 ml) and water (2×50 ml), dried on sodium sulphate, filtered and the solvent is evaporated under reduced pressure. 500 mg of the more polar diastereoisomer of 2-(3-phenyl-3-bromopropyl)-3-carboethoxy-5-cyano-6-methyl -4-(m-nitrophenyl)-1,4-dihydropyridine are obtained as an amorphous solid.

Workup

  1. extractionextracted with diethyl ether (25 ml)
  2. customThe phases are separated
  3. washthe organic one is washed with a 5% NaHCO3 aqueous solution (3×50 ml) and water (2×50 ml)
  4. customdried on sodium sulphate
  5. filtrationfiltered
  6. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-bc351af11a4642f28b3c6fde6ca989b1
Source dataset
uspto-grants-1991_12
Patent number
US05075324

Reaction notes

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