Ethanol → N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamide

HRID 511879

Reaction equation

HRID 511879 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH:12][C:13](=[O:16])[CH2:14][CH3:15].[CH2:17](O)C>ClCCl.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]([CH3:17])[C:13](=[O:16])[CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 702EthanolHCID 2176144N-(2-methoxy-5-nitrophenyl)propanamide

Product 1

HCID 59167877N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamideYield 31%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 340 mg of N1-(2-methaxy-5-nitrophenyl)-N1, N2, N2-trimethylethane-1,2-diamine (2) in 20 mL of ethanol containing 5% w/w of Pd—C (10%) was subjected to hydrogenation (1 atm, balloon) for 1.5 h. The contents of the flask were passed through a short pad of celite and washed with MeOH. The filtrate was evaporated under reduced pressure and crude amine obtained was carried over to the next reaction without further purification. Thiocarbodiimidazole (260 mg, 1.46 mmol) was added to the crude amine in dichloromethane (10 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 h, and concentrated. The crude product was then purified by flash chromatography on silica gel to give N1-(5-isothiocyanato-2-methoxyphenyl)-)-N1, N2, N2-trimethylethane-1,2-diamine (3) (110 mg, 0.42 mmol, 31%).

Workup

  1. washwashed with MeOH
  2. customThe filtrate was evaporated under reduced pressure and crude amine
  3. customobtained
  4. customwas carried over to the next reaction without further purification
  5. concentrationconcentrated
  6. customThe crude product was then purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-20b46d084097407981a55ad2c4758bf3
Source dataset
uspto-grants-2015_08
Patent number
US09101614B2

Linked notes

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