Hydrochloric Acid → 4-[(6a-Methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoic acid

HRID 1097393Notes

Reaction equation

HRID 1097393 reaction equation
[CH3:1][C:2]12[C:14]3[C:6](=[CH:7][C:8]([NH:15][C:16]4[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=4)=[CH:9][C:10]=3[CH2:11][CH2:12][CH2:13]1)[CH2:5][CH2:4][CH2:3]2.[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]12[C:14]3[C:10](=[CH:9][C:8]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=4)=[CH:7][C:6]=3[CH2:5][CH2:4][CH2:3]1)[CH2:11][CH2:12][CH2:13]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25190221Ethyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

Product 1

HCID 251902204-[(6a-Methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoic acidYield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of ethyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate (0.250 g) in ethanol (15 ml) was added with 20% aqueous sodium hydroxide (5 ml), and the mixture was stirred overnight at room temperature. The reaction mixture was 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 ethyl acetate-n-hexane to obtain the title compound (0.185 g, yield: 80%) as pale brown needles (melting point: 232-234° C.).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resulting residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-a621ec11f7fc47beba1b58ef9589b914
Source dataset
uspto-grants-2012_03
Patent number
US08143260B2

Reaction notes

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