Hydrochloric Acid → HCID 22388197, compound

HRID 1699822Notes

Reaction equation

HRID 1699822 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[C:4]([C:6]1[N:14]2[C:9]([CH:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:13]2)=[CH:8][C:7]=1[CH3:19])=O.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[CH2:4][C:6]1[N:14]2[C:9]([CH:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:13]2)=[CH:8][C:7]=1[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22388159HCID 22388159, compound

Product 1

HCID 22388197HCID 22388197, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(2,4-dichlorobenzoyl)-2-methylindolizine-6-carboxylate (2.34 g) in tetrahydrofuran (47 ml) was dropwise added a borane-dimethylsulfide complex (10.0 M, 6.5 ml) under ice-cooling. The mixture was stirred for 4 hr at room temperature. To this reaction mixture was carefully added dropwise 1N hydrochloric acid (6.5 ml) under ice-cooling, and the mixture was stirred for 30 min at room temperature. The reaction mixture was neutralized with saturated aqueous sodium hydrogencarbonate solution, and the resulting product was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the objective compound (490.4 mg) as a pale-yellow solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 30 min at room temperature
  4. extractionthe resulting product was extracted three times with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-350f07445eb047469372c24112e1ecd7
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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