Ethanol → HCID 19363278, compound

HRID 850511Notes

Reaction equation

HRID 850511 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([N:9]([CH2:21][C:22]([O:24]CC)=O)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[O:8])=[C:5]([N+:29]([O-])=O)[C:4]=1[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C(O)C.[H][H].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C].[Pd].C1(C)C=CC=CC=1>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][N:9]2[C:7](=[O:8])[C:6]3[CH:27]=[CH:28][C:3]([O:2][CH3:1])=[C:4]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:5]=3[NH:29][C:22](=[O:24])[CH2:21]2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 54551452HCID 54551452, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19363278HCID 19363278, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 1140TolueneSolvent

Procedure

Ethyl {(4-Methoxy-2-nitro-3-pentyloxybenzoyl)-[2-(4-nitrophenyl)-ethyl]amino}acetate (70.0 mg, 0.135 mmol) and ethanol (2 ml) were mixed, and 10% palladium-carbon catalyst was added. The reaction mixture was stirred in a stream of hydrogen at room temperature for 10.5 hours, and then filtered. The filtrate was concentrated under reduced pressure. Toluene (10 ml) and p-toluene sulfonate monohydrate (1 mg, 0.0053 mmol) were added to the precipitated crude crystals, and the mixture was refluxed under heating for 3.5 hours. Ethyl acetate (20 ml) was added to this reaction mixture, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (5 ml) and saturated brine (5 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (chloroform/methanol=10/1) to give 4-[2-(4-aminophenyl)ethyl]-8-methoxy-9-pentyloxy-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (35 mg, 63% in 2 steps) as colorless crystals.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customprecipitated crude crystals
  4. temperaturethe mixture was refluxed
  5. temperatureunder heating for 3.5 hours
  6. additionEthyl acetate (20 ml) was added to this reaction mixture
  7. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (5 ml) and saturated brine (5 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe drying agent was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe obtained residue was purified by column chromatography on silica gel (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-9f406abaa711433793964fdd1ade6a85
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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