Ethyl Acetate → HCID 10778001, compound

HRID 840253Notes

Reaction equation

HRID 840253 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15](O)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1.S(Cl)([Cl:20])=O.CCOC(C)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([Cl:20])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 10490611HCID 10490611, compound

Product 1

HCID 10778001HCID 10778001, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 13.3 g (54 mmol) of 8-chloro-6,11-dihydro-11-hydroxy-5H-benzo[5,6]cyclohepta[1,2-b]pyridine in 290 mL of toluene at −15° C. and under an atmosphere of nitrogen was added via syringe pump over a period of 1 hour 6.20 mL (85.7 mmol) of thionyl chloride. The extent of reaction was monitored by TLC (50% EtOAc in hexanes). When completed the mixture was poured into 300 mL of 1.0 N aqueous NaOH and extracted with EtOAc (5×). The combined organic portions were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was taken up in EtOAc, quickly filtered through basic alumina, and concentrated again to yield a product which was triturated with pentane to yield 10.22 g of the title compound as a tan solid.

Workup

  1. customThe extent of reaction
  2. extractionextracted with EtOAc (5×)
  3. washThe combined organic portions were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationquickly filtered through basic alumina
  8. concentrationconcentrated again
  9. customto yield a product which
  10. customwas triturated with pentane

Sources & evidence

ORD record
ord-3c06b933c7d24921a6372c0fc159379a
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

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