Water → HCID 13194169, compound

HRID 434711Notes

Reaction equation

HRID 434711 reaction equation
[CH3:1][C:2]12[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]([NH:7]1)[CH2:5][C:4]1[CH:14]=[C:15]([O:18]C)[CH:16]=[CH:17][C:3]2=1.Cl.[NH+]1C=CC=CC=1.O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[CH3:1][C:2]12[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]([NH:7]1)[CH2:5][C:4]1[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:3]2=1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 13194168HCID 13194168, compoundHCID 21584435Pyridinium hydrochloride

Product 1

HCID 13194169HCID 13194169, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-methoxy-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (2.7 g, 0.0107 mol) and pyridinium hydrochloride (16.2 g) is stirred at 200° for 2 hours. The melt is cooled to 50° C. and slurried with water (75 ml). The slurry is made basic with aqueous saturated NaHCO3 and extracted with ether (3×100 ml). The combined extracts are dried over MgSO4 and filtered, and the filtrate evaporated to dryness under reduced pressure to give 2.19 g of crude product. Column chromatography (silica gel with 2% methanol in chloroform) provides a solid which is recrystallized from ethyl acetate to give 1.20 g (47%) of pure title compound; m.p. 215°-217° C.

Workup

  1. extractionextracted with ether (3×100 ml)
  2. dry with materialThe combined extracts are dried over MgSO4
  3. filtrationfiltered
  4. customthe filtrate evaporated to dryness under reduced pressure
  5. customto give 2.19 g of crude product
  6. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1c419b73e1ee4d3aaf4345b1e1f1f06e
Source dataset
uspto-grants-1983_08
Patent number
US04399141

Reaction notes

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