Hydrochloric Acid → HCID 21477008, compound

HRID 2293555Notes

Reaction equation

HRID 2293555 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH:13][C:14](=O)[CH2:15][CH3:16])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH:13][CH2:14][CH2:15][CH3:16])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21476993HCID 21476993, compound

Product 1

HCID 21477008HCID 21477008, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of argon, 4.80 g of methyl 2-methoxy-4-propanoylaminobenzoate was dissolved in 50 ml of tetrahydrofuran and, at room temperature, 1.9 ml (20.2 mmol) of borane dimethylsulfide complex was added in small portions. After 1 hour of reflux, and excess reagent was decomposed with dilute hydrochloric acid under ice-cooling. The reaction solution was extracted with chloroform, the resulting organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under a reduced pressure. Then, the resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to give 3.19 g of methyl 2-methoxy-4-propylaminobenzoate. Next, in an atmosphere of argon, this compound and 2.5 ml of pyridine were dissolved in 50 ml of methylene chloride, and 2.1 ml of anhydrous trifluoroacetic acid was slowly added dropwise under ice-cooling. After 12 hours of stirring at room temperature, the reaction solution was poured in ice water, stirred for a while and then extracted with methylene chloride. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under a reduced pressure. Then, the resulting residue was purified by silica gel column chromatography (chloroform:methanol=200:1) to give 3.88 g of methyl 2-methoxy-4-(propyltrifluoroacetyl)aminobenzoate.

Workup

  1. addition1.9 ml (20.2 mmol) of borane dimethylsulfide complex was added in small portions
  2. temperatureAfter 1 hour of reflux
  3. temperaturecooling
  4. extractionThe reaction solution was extracted with chloroform
  5. washthe resulting organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThen, the resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-7bdbc7a260544845b13e02b12241966f
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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