HCID 69280722, compound → HCID 69282522, compound

HRID 1293487Notes

Reaction equation

HRID 1293487 reaction equation
C[O:2][C:3]([C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:18])[CH:15]=3)[N:10]([CH3:19])[C:9]=2[C:8]([O:20][CH3:21])=[CH:7][CH:6]=1)=[O:4]>CO.[OH-].[Na+]>[Cl:18][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:19])[C:9]1[C:8]([O:20][CH3:21])=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:17]2=1

Participants

4

Reactant 1

HCID 69280722HCID 69280722, compound

Product 1

HCID 69282522HCID 69282522, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of methyl-6-chloro-1-methoxy-9-methyl-9H-4-carbazole carboxylate (390 mg 1.285 mmoles) in 20 mL methanol, 5 mL of 10% sodium hydroxide solution was added and stirred for 3 hrs. Methanol from the reaction mixture was evaporated under reduced pressure, diluted with ethyl acetate (5 mL) and washed with 10% sodium hydroxide solution (2×2 mL). This aqueous layer is acidified with 1N HCl and extracted with ethyl acetate (2×25 mL), dried over sodium sulfate and concentrated to give 350 of the title compound

Workup

  1. customMethanol from the reaction mixture was evaporated under reduced pressure
  2. additiondiluted with ethyl acetate (5 mL)
  3. washwashed with 10% sodium hydroxide solution (2×2 mL)
  4. extractionextracted with ethyl acetate (2×25 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e4fe7bb16e414141ada9a63fcd740f2d
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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