Hydrochloric Acid → HCID 21841497, compound

HRID 1739570Notes

Reaction equation

HRID 1739570 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8]([C:10]([N:12]([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])=[O:11])[CH:7]=[C:6]([N+:19]([O-:21])=[O:20])[C:5]=1[C:22]1[CH:27]=[CH:26][C:25]([C:28]([O:30]C)=[O:29])=[CH:24][CH:23]=1.Cl>O1CCCC1.O>[NH2:3][C:4]1[CH:9]=[C:8]([C:10]([N:12]([CH:16]([CH3:17])[CH3:18])[CH:13]([CH3:15])[CH3:14])=[O:11])[CH:7]=[C:6]([N+:19]([O-:21])=[O:20])[C:5]=1[C:22]1[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21841476HCID 21841476, compound

Product 1

HCID 21841497HCID 21841497, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.64 ml of 2N sodium hydroxide were added to a solution of 235 mg of product A in 4 ml of tetrahydrofuran and the mixture was heated under refluxed for 2 hours. Then, the reaction mixture was diluted with 10 ml of water and the pH was adjusted to 9 with 1N hydrochloric acid. Washing was carried out with ethyl acetate and the pH is adjusted to 5 with 1N hydrochloric acid. Extraction was carried out with ether and the ethereal phases were dried with MgSO4, followed by evaporation under reduced pressure. The residue was crystallized from ether to obtain 191.7 mg of the expected product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxed for 2 hours
  3. washWashing
  4. extractionExtraction
  5. dry with materialthe ethereal phases were dried with MgSO4
  6. customfollowed by evaporation under reduced pressure
  7. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-fb3b81b031c144c09196f855f963c608
Source dataset
uspto-grants-1999_10
Patent number
US05965763

Reaction notes

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