Ethyl Acetate → HCID 10778001, compound

HRID 1379660Notes

Reaction equation

HRID 1379660 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.C(OCC)(=O)C.[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% ethyl acetate in hexanes). When completed the mixture was poured into 300 mL of 1.0N aqueous NaOH and extracted with ethyl acetate (5X). The combined organic portions were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was taken up in ethyl acetate, 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 ethyl acetate (5X)
  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-d1a3e1c03e154bc7abb515473a4eab2e
Source dataset
uspto-grants-1997_09
Patent number
US05672611

Reaction notes

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