Sodium Hydroxide → HCID 15818737, compound

HRID 2259306Notes

Reaction equation

HRID 2259306 reaction equation
ClCC([O:5][C:6]1[CH:14]=[CH:13][C:12]2[N:11]([CH3:15])[C:10]3[C:16](=[O:19])[CH2:17][CH2:18][C:9]=3[C:8]=2[CH:7]=1)=O.[OH-].[Na+]>CCO>[OH:5][C:6]1[CH:14]=[CH:13][C:12]2[N:11]([CH3:15])[C:10]3[C:16](=[O:19])[CH2:17][CH2:18][C:9]=3[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19003099HCID 19003099, compound

Product 1

HCID 15818737HCID 15818737, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Chloroacetyloxy-1,4-dihydro-4-methylcyclopent[b]indol-3(2H)-one (5.0 g) was suspended in EtOH (100 ml), and thereafter 10% NaOH solution (50 ml) was added and the mixture was stirred at room temperature for 3 hours. The mixture was concentrated in vacuo, CH2Cl2 (100 ml) was added followed by 10% HCl until the aqueous layer was neutralized. The layers were separated and the aqueous phase extracted with CH2Cl2 (2×100 ml). The organic portion was dried (Na2SO4) and concentrated and the residue was recrystallized from 95% EtOH to provide 1,4-dihydro-7-hydroxy-4-methylcyclopent[b]indol-3(2H)-one as an off-white solid. The phenol was dissolved in CH2Cl2 (100 ml), and thereafter 1,8-diazabicyclo[5.4.0]undec-7-ene (0.4 g) was added followed by methyl isocyanate (1.4 g) and the mixture was stirred overnight. The mixture was concentrated in vacuo to afford an oily solid which was crystallized front EtOH to provide 1,4-dihydro-7-methylaminocarbonyloxy-4-methylcyclopent[b] indol-3(2H)-one (1.1 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo, CH2Cl2 (100 ml)
  2. additionwas added
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with CH2Cl2 (2×100 ml)
  5. dry with materialThe organic portion was dried (Na2SO4)
  6. concentrationconcentrated
  7. customthe residue was recrystallized from 95% EtOH

Sources & evidence

ORD record
ord-5ea07b4635ec4ecc81e49a981b135df2
Source dataset
uspto-grants-1995_12
Patent number
US05472975

Reaction notes

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