Hydrochloric Acid → HCID 13704349, compound

HRID 1719703Notes

Reaction equation

HRID 1719703 reaction equation
C([NH:4][C:5]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:8]2[O:9][C:10]([CH3:21])([CH3:20])[C@@H:11]([OH:19])[C@H:12]([N:13]3[CH2:17][CH2:16][CH2:15][C:14]3=[O:18])[C:7]=2[CH:6]=1)(=O)C.Cl.C(O)C>O.[OH-].[Na+]>[NH2:4][C:5]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:8]2[O:9][C:10]([CH3:20])([CH3:21])[C@@H:11]([OH:19])[C@H:12]([N:13]3[CH2:17][CH2:16][CH2:15][C:14]3=[O:18])[C:7]=2[CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 13704345HCID 13704345, compound

Product 1

HCID 13704349HCID 13704349, compoundYield 113.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

The compound of Example 1 (130 mg), 5N HCl (5 ml) and ethanol (9 ml) were heated under reflux for 3 h. After cooling, the reaction mixture was diluted with water and basified with dilute sodium hydroxide solution, extracted with ethyl acetate, and dried with anhydrous magnesium sulphate. Removal of drying agent and evaporation gave a red solid (130 mg). Recrystallisation from ethyl acetate-pentane gave the nitroamine (40 mg) as brick red crystals of m.p. 244°-245° C.

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with anhydrous magnesium sulphate
  5. customRemoval
  6. customof drying
  7. customagent and evaporation

Sources & evidence

ORD record
ord-d42caeccc75a4dc0a0f29119282d1096
Source dataset
uspto-grants-1985_09
Patent number
US04542149

Reaction notes

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