Sodium Hydroxide → HCID 66700091, compound

HRID 1910724Notes

Reaction equation

HRID 1910724 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[C:9]3[CH:16]=[CH:15][N:14](S(C4C=CC(C)=CC=4)(=O)=O)[C:10]3=[CH:11][CH:12]=2)[CH:7]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[CH2:6][CH:5]1[CH3:35])(=[O:3])[CH3:2].[OH-].[Na+].[Cl-].[NH4+]>CO>[C:1]([N:4]1[C:13]2[C:8](=[C:9]3[CH:16]=[CH:15][NH:14][C:10]3=[CH:11][CH:12]=2)[C@H:7]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[CH2:6][C@@H:5]1[CH3:35])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 66699966HCID 66699966, compound

Product 1

HCID 66700091HCID 66700091, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

[Step 4] 9.5 mg of the 6-acetyl-9-(4-chlorophenylamino)-7-methyl-3-tosyl-6,7,8,9-tetrahydro-3H-pyrrolo[3.2-f]quinoline were dissolved in methanol (1 mL) followed by adding 4 M aqueous sodium hydroxide solution (1 mL) and stirring for 30 minutes at 80° C. After allowing to cool to room temperature, the reaction liquid was neutralized by addition of saturated aqueous ammonium chloride solution followed by extracting with chloroform, washing the organic layer with saturated brine, dehydrating with anhydrous sodium sulfate and concentrating under reduced pressure. The resulting residue was purified by PLC (chloroform:methanol=20:1) to obtain 3.8 mg of the target compound in the form of a yellow oil (59.4%).

Workup

  1. temperatureto cool to room temperature
  2. customthe reaction liquid
  3. extractionby extracting with chloroform
  4. washwashing the organic layer with saturated brine
  5. concentrationconcentrating under reduced pressure
  6. customThe resulting residue was purified by PLC (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-68f0fd93d60948d68f44b057e47ce24c
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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