Hydrochloric Acid → HCID 66811177, compound

HRID 1097384Notes

Reaction equation

HRID 1097384 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]1[N:20]=[CH:19][C:18]([C:21]([O:23]CC)=[O:22])=[CH:17][N:16]=1.[OH-].[Na+].Cl>C(O)C>[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]1[N:16]=[CH:17][C:18]([C:21]([OH:23])=[O:22])=[CH:19][N:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66811056HCID 66811056, compound

Product 1

HCID 66811177HCID 66811177, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl 2-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]pyrimidine-5-carboxylate (0.055 g) in ethanol (5 ml) was added with 20% aqueous sodium hydroxide (1 ml), and the mixture was stirred at 50° C. for 3 hours. The reaction mixture was left to cool and then made acidic with 2 N aqueous hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was recrystallized from ethanol-chloroform to obtain the title compound (0.045 g, yield: 90%) as colorless needles (melting point: 296-298° C.).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe resulting residue was recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-5aed94b785d5444fbf5796a0341a0c30
Source dataset
uspto-grants-2012_03
Patent number
US08143260B2

Reaction notes

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