Hydrochloric Acid → HCID 12891348, compound

HRID 224277Notes

Reaction equation

HRID 224277 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH3:15][NH:16][C:17]([C:19]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH:20]1[C:22](N)=O)=O.[H-].[OH-].[Na+].[ClH:34]>C1C=CC=CC=1.O.C(O)C.CCOCC>[ClH:34].[CH3:15][N:16]1[CH2:22][CH:20]2[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([CH2:21]2)[CH2:17]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 166653HydrideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 23332346HCID 23332346, compound

Product 1

HCID 12891348HCID 12891348, compound

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 30 ml of sodium bis(2-methoxyethoxy)aluminum hydride (70% benzene solution) is added dropwise a solution of 5.5 g of N-methyl-1-phenyl-1,2-cyclopropanedicarboxamide (U.S. Pat. No. 3,166,571-Ex. 1) in 400 ml of benzene over a one hour period at room temperature under nitrogen. The mixture is heated at reflux under nitrogen for 90 minutes. The excess hydride reagent is decomposed by the cautious addition of 25 ml of 10 N sodium hydroxide and then diluted to 200 ml with water. The benzene phase is separated and the aqueous phase is extracted with chloroform. The combined organic phases are dried over magnesium sulfate and concentrated under reduced pressure giving a liquid. The liquid is dissolved in ethanol and acidified with 15 ml of 2.3 N ethanolic hydrogen chloride. The addition of ether causes the formation of a solid which is recrystallized from isopropyl alcohol-hexane giving white crystals, m.p. 158°-160° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux under nitrogen for 90 minutes
  3. customThe benzene phase is separated
  4. extractionthe aqueous phase is extracted with chloroform
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customgiving a liquid
  8. customis recrystallized from isopropyl alcohol-hexane giving white crystals, m.p. 158°-160° C.

Sources & evidence

ORD record
ord-7b40966cc8e44493966858f510ab0285
Source dataset
uspto-grants-1980_11
Patent number
US04231935

Reaction notes

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