Hydrochloric Acid → HCID 58526575, compound

HRID 1097378Notes

Reaction equation

HRID 1097378 reaction equation
[CH3:1][N:2]([C:13]1[CH:24]=[C:23]2[C:25]3[CH:19]([CH2:20][CH2:21][CH2:22]2)[CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][N:2]([C:13]1[CH:24]=[C:23]2[C:25]3[CH:19]([CH2:20][CH2:21][CH2:22]2)[CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=1)[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58526560HCID 58526560, compound

Product 1

HCID 58526575HCID 58526575, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of methyl 4-[N-methyl-(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate (0.033 g) in ethanol (10 ml) was added with 20% aqueous sodium hydroxide (1 ml), and the mixture was stirred overnight at 50° C. The reaction mixture was left to cool and then made acidic with 2 N aqueous hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was recrystallized from ethanol-chloroform to obtain the title compound (0.027 g, yield: 87%) as colorless needles (melting point: 288-289° C.).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe resulting residue was recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-2d04545a4534426bbb866fd34462832a
Source dataset
uspto-grants-2012_03
Patent number
US08143260B2

Reaction notes

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