Hydrochloric Acid → HCID 19010336, compound

HRID 1741622Notes

Reaction equation

HRID 1741622 reaction equation
OC(C)(C)[C:3]#[C:4][C:5]1[CH:6]=[N:7][C:8]([C:15]2[NH:16][C:17](=[O:24])[C:18]([CH:21]([CH3:23])[CH3:22])([CH3:20])[N:19]=2)=[C:9]([CH:14]=1)[C:10]([O:12]C)=[O:11].[OH-].[Na+].Cl>O>[C:4]([C:5]1[CH:6]=[N:7][C:8]([C:15]2[NH:16][C:17](=[O:24])[C:18]([CH:21]([CH3:22])[CH3:23])([CH3:20])[N:19]=2)=[C:9]([CH:14]=1)[C:10]([OH:12])=[O:11])#[CH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86748033HCID 86748033, compound

Product 1

HCID 19010336HCID 19010336, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.5 g of 5-(3-hydroxy-3-methyl-1-butynyl)-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid, methyl ester, and 0.185 g of sodium hydroxide in 12 mL water is heated at reflux for 21/2 hours, then stirred at room temperature overnight. The reaction is then cooled to 10°, acidified to pH 3 with concentrated hydrochloric acid and extracted with methylene chloride. The organic phase is dried and concentrated in vacuo to afford the crude, desired product. An analytical sample, purified via its methyl ester, had mp 190°-195°.

Workup

  1. temperatureat reflux for 21/2 hours
  2. temperatureThe reaction is then cooled to 10°
  3. extractionextracted with methylene chloride
  4. customThe organic phase is dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2148b27e1b64acca8d91e1e578a911b
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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