Hydrochloric Acid → Methyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carbamoyl]benzoate

HRID 1517497Notes

Reaction equation

HRID 1517497 reaction equation
[CH3:1][C:2]12[C:14]3[C:6](=[CH:7][C:8]([NH2:15])=[CH:9][C:10]=3[CH2:11][CH2:12][CH2:13]1)[CH2:5][CH2:4][CH2:3]2.[Cl-].[C:17]([O:28][CH3:29])(=[O:27])[C:18]1[CH:26]=[CH:25][C:21]([C:22]([O-])=[O:23])=[CH:20][CH:19]=1.Cl>C1C=CC=CC=1.N1C=CC=CC=1>[CH3:1][C:2]12[C:14]3[C:6](=[CH:7][C:8]([NH:15][C:22]([C:21]4[CH:25]=[CH:26][C:18]([C:17]([O:28][CH3:29])=[O:27])=[CH:19][CH:20]=4)=[O:23])=[CH:9][C:10]=3[CH2:11][CH2:12][CH2:13]1)[CH2:5][CH2:4][CH2:3]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 22493623Monomethyl terephthalate chlorideHCID 58420583HCID 58420583, compound

Product 1

HCID 67391032Methyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carbamoyl]benzoateYield 82.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

A solution of 6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenylamine (0.138 g) in anhydrous benzene (5 ml) and pyridine (2 ml) was added with monomethyl terephthalate chloride (0.177 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with 2 N aqueous hydrochloric acid and thereby made acidic, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, 10% aqueous sodium carbonate, water and saturated brine, and then dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was recrystallized from chloroform-n-hexane to obtain the title compound (0.205 g, yield: 82%) as colorless needles (melting point: 217-218° C.).

Workup

  1. extractionmade acidic, and the mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water, 10% aqueous sodium carbonate, water and 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 chloroform-n-hexane

Sources & evidence

ORD record
ord-b52cbe65716e4d1b8d42deff5cf4efa8
Source dataset
uspto-grants-2012_07
Patent number
US08232300B2

Reaction notes

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