Sodium Hydroxide → HCID 178439625, compound

HRID 887927Notes

Reaction equation

HRID 887927 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9](Cl)=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:14]([NH2:16])=O)(=O)C.[OH-].[Na+].C([O-])(O)=O.[Na+]>Cl>[CH2:6]([C:5]1[N:4]=[C:14]([C@@H:5]2[CH2:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:4]2)[NH:16][CH:14]=1)[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 21914132HCID 21914132, compound

Product 1

HCID 178439625HCID 178439625, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

Compound (8) (0.00170 mol) was dissolved in HCl, 6N (20 ml), and immediately warmed in an oil bath at 100° C. under nitrogen for 200 minutes. The heat was turned off, and the sample was cooled to 0° C. 3 N NaOH (35 ml) was slowly added. Basification was completed with saturated NaHCO3. The sample was extracted with chloroform. The combined organic phases were dried, filtered, and the resulting solution was used without further purification in further synthesis, yielding (S)-2,3-dihydro-2-(4-propyl-1H-imidazol-2-yl)-1H-indole (intermediate 5).

Workup

  1. temperaturethe sample was cooled to 0° C
  2. extractionThe sample was extracted with chloroform
  3. customThe combined organic phases were dried
  4. filtrationfiltered
  5. customthe resulting solution was used without further purification in further synthesis

Sources & evidence

ORD record
ord-64fcb0d6eaf0454fb6446d2e24eba7b5
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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