HCID 69282516, compound → HCID 69282503, compound

HRID 1293484Notes

Reaction equation

HRID 1293484 reaction equation
C[O:2][C:3]([C:5]1[C:17]2[C:16]3[C:11](=[C:12]([Cl:18])[CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:9]=2[C:8]([O:26][CH3:27])=[CH:7][CH:6]=1)=[O:4]>CO.[OH-].[Na+]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[N:10]([CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[C:9]1[C:8]([O:26][CH3:27])=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:17]2=1

Participants

4

Reactant 1

HCID 69282516HCID 69282516, compound

Product 1

HCID 69282503HCID 69282503, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of methyl-8-chloro-9-cyclohexylmethyl-1-methoxy-9H-4-carbazole carboxylate (95 mg 0.2464 mmoles) in 5 mL methanol, 2 mL of 10% sodium hydroxide solution was added and refluxed for 3 hrs. Methanol from the reaction mixture was evaporated under reduced pressure, diluted with ethyl acetate (50 mL) and washed with 10% sodium hydroxide solution (2×20 mL), this aqueous layer was acidified with 1N HCl and extracted with ethyl acetate (2×25 mL), dried over sodium sulfate and concentrated to give 90 mg of the title compound.

Workup

  1. temperaturerefluxed for 3 hrs
  2. customMethanol from the reaction mixture was evaporated under reduced pressure
  3. additiondiluted with ethyl acetate (50 mL)
  4. washwashed with 10% sodium hydroxide solution (2×20 mL)
  5. extractionextracted with ethyl acetate (2×25 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-280a572b4b5d4e89a80f2dcb39fc9071
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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