Triethylamine → Ethyl [(2-amino-6-methoxybenzyl)-(4-chlorobenzoyl)amino]acetate

HRID 2417510Notes

Reaction equation

HRID 2417510 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]([N+:17]([O-])=O)[CH:6]=[CH:5][CH:4]=1.[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.C(N(CC)CC)C.[H][H]>ClCCl.C(OCC)(=O)C.[Pd]>[NH2:17][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[CH2:9][N:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([Cl:20])=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 86589881Ethyl (6-methoxy-2-nitrobenzyl)aminoacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 86589882Ethyl [(2-amino-6-methoxybenzyl)-(4-chlorobenzoyl)amino]acetate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5.6 g (21.3 mmol) of ethyl (6-methoxy-2-nitrobenzyl)aminoacetate was dissolved in 50 ml of dichloromethane. 3.3 ml (25.2 mmol) of 4-chlorobenzoyl chloride and 4.4 ml (32 mmol) of triethylamine were added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the crude product was obtained. The crude product was dissolved in 50 ml of ethyl acetate. 520 mg of 10% palladium/carbon was added to the obtained solution and they were stirred in the presence of hydrogen at room temperature for 4 hours. The reaction mixture was filtered through Celite. The solvent was evaporated to obtain the crude product, which was then purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. temperatureunder cooling with ice for 2 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. customThe solvent was evaporated
  5. customto obtain the crude product, which
  6. customwas then purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-b9298683e2164288a38850700b4f4c37
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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