Sodium Hydroxide → HCID 11653874, compound

HRID 2236107Notes

Reaction equation

HRID 2236107 reaction equation
[C:1]([N:9]1[CH2:27][CH2:26][C:12]2[N:13]([CH2:20][C:21]([O:23]CC)=[O:22])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=2[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.O>[C:2]1([C:1]([N:9]2[CH2:27][CH2:26][C:12]3[N:13]([CH2:20][C:21]([OH:23])=[O:22])[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:11]=3[CH2:10]2)=[O:8])[C:7]2[C:6](=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71552330HCID 71552330, compound

Product 1

HCID 11653874HCID 11653874, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step b): A solution of crude ethyl (2-benzoyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate (0.085 mmol) in THF (0.5 ml) is treated with 0.2 N aqueous NaOH solution (0.64 ml) at rt for 15 min. Then, the yellow reaction mixture is diluted with water (2 ml), washed with diethyl ether (2 ml), acidified with conc. HCl to pH 1 and extracted with dichloromethane. The combined organic phases are washed with water, then dried over Na2SO4, filtered and the solvent evaporated. The crude product is recrystallized from diisopropyl ether to give pure title compound as yellow solid: tR (LC-1) 2.95 min; ESI-MS positive ion): m/z 335.17 [M+H]+ (calcd 334.37 for C20H18N2O3).

Workup

  1. washwashed with diethyl ether (2 ml)
  2. extractionextracted with dichloromethane
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe crude product is recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-94a0b99ee57d44ae815ec6f6a0002ff4
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

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