Hydrochloric Acid → HCID 67391539, compound

HRID 1517490Notes

Reaction equation

HRID 1517490 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][N: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:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][N:18]=1)=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67391040HCID 67391040, compound

Product 1

HCID 67391539HCID 67391539, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of methyl 6-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carbamoyl]nicotinate (0.194 g) in ethanol (10 ml) was added with 2 N aqueous sodium hydroxide (2 ml), and the mixture was stirred at room temperature for 2 hours. 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 (0.161 g, yield: 87%) as pale yellow needles (melting point: 252-253° 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-77918f4539d841b7948cf57e2c1581e7
Source dataset
uspto-grants-2012_07
Patent number
US08232300B2

Reaction notes

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