Hydrochloric Acid → HCID 13704349, compound

HRID 236421Notes

Reaction equation

HRID 236421 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-1256fa9abcec4e2ca176a2d0d68a7b29
Source dataset
uspto-grants-1987_02
Patent number
US04644070

Reaction notes

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