Diisopropylethylamine → N-methyl-2-(3-nitrophenoxy)acetamide

HRID 76446Notes

Reaction equation

HRID 76446 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[O:7][CH2:8][C:9](OCC)=[O:10])([O-:3])=[O:2].Cl.CN.[CH:20]([N:23](C(C)C)CC)(C)C>CO.O>[CH3:20][NH:23][C:9](=[O:10])[CH2:8][O:7][C:6]1[CH:14]=[CH:15][CH:16]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2741030Ethyl 2-(3-nitrophenoxy)acetateHCID 6364545Methylamine hydrochloride

Product 1

HCID 7865111N-methyl-2-(3-nitrophenoxy)acetamideYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 3-nitrophenoxyacetate (9.12 g, 40 mmol), methylamine hydrochloride (26.8 g, 400 mmol) and diisopropylethylamine (35.5 mL, 200 mL) in MeOH (100 mL) was stirred in a pressure vial at 90° C. for 6 h. The reaction was cooled to room temperature, diluted with water (1 liter), the solid formed was filtered, washed with water and dried to get the desired N-methyl 3-nitrophenoxyacetamide (8 g, 95%). 1H NMR CDCl3): δ 7.91 (dd, 1H, J=1.8 and 8.1 Hz), 7.78 (t, 1H, J=2.4 Hz), 7.50 (t, 1H, J=8.7 Hz), 7.29 (dd, 1H, J=1.8 and 8.4 Hz), 6.50 (bs, 2H), 4.57 (s, 2H), 2.95 and 2.93 (2s, 3H); LCMS: ret. time: 17.54 min.; purity: 100%; MS (m/e): 211 (MH+).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe solid formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0f84ce4e713643ba9b7da1fbfe2e5c43
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Reaction notes

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