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

HRID 1517489Notes

Reaction equation

HRID 1517489 reaction equation
[CH:1]1[C:12]2=[C:13]3[CH:8]([CH2:9][CH2:10][CH2:11]2)[CH2:7][CH2:6][CH2:5][C:4]3=[CH:3][C:2]=1[NH:14][C:15]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=1)=[O:16].[OH-].[Na+].Cl>C(O)C>[CH:3]1[C:4]2=[C:13]3[CH:8]([CH2:7][CH2:6][CH2:5]2)[CH2:9][CH2:10][CH2:11][C:12]3=[CH:1][C:2]=1[NH:14][C:15]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=1)=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67391601HCID 67391601, compound

Product 1

HCID 673911074-[(5,6,6a,7,8,9-Hexahydro-4H-2-phenalenyl)carbamoyl]benzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of methyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carbamoyl]benzoate (0.093 g) in ethanol (10 ml) was added with 2 N aqueous sodium hydroxide (3 ml), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was made acidic with 2 N aqueous hydrochloric acid, and 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 (0.080 g, yield: 90%) as colorless prisms (melting point: 283-284° C.).

Workup

  1. extractionextracted 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-277e1b9590af4bf0a69f9eab9887cdbe
Source dataset
uspto-grants-2012_07
Patent number
US08232300B2

Reaction notes

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