Hydrochloric Acid → HCID 66795184, compound

HRID 1012318Notes

Reaction equation

HRID 1012318 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:30]=[CH:29][C:28]([C:31]([O:33]C)=[O:32])=[CH:27][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[ClH:37]>O1CCCC1.CO>[ClH:37].[CH:1]1([C:7]2[C:8]3[CH:30]=[CH:29][C:28]([C:31]([OH:33])=[O:32])=[CH:27][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23152384HCID 23152384, compound

Product 1

HCID 66795184HCID 66795184, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 12-cyclohexyl-4-(pyridin-3-yl)-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (130 mg, 0.203 mmol) in tetrahydrofuran (2 ml) and methanol (2 ml) was added 4N aqueous sodium hydroxide solution (1 ml), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was adjusted to pH 6.5 with 2N hydrochloric acid, and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. To a solution of the residue in chloroform was added 4N HCl-ethyl acetate solution (0.5 ml), and the solvent was evaporated under reduced pressure. A mixed solvent (hexane:ethyl acetate=4:1) was added to the residue. The precipitated solid was collected by filtration to give 12-cyclohexyl-4-(pyridin-3-yl)-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylic acid hydrochloride (88 mg, yield 91%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. additionTo a solution of the residue in chloroform was added 4N HCl-ethyl acetate solution (0.5 ml)
  7. customthe solvent was evaporated under reduced pressure
  8. additionA mixed solvent (hexane:ethyl acetate=4:1) was added to the residue
  9. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-46fb6254b52744cdbb4d77b5851e5425
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

Loading…