N-Methyl-4-nitroaniline → HCID 66877507, compound

HRID 2281463Notes

Reaction equation

HRID 2281463 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([NH:8][CH3:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(CC)CC.[CH2:19]([O:26][CH2:27][C:28](Cl)=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl.CCOC(C)=O>[CH2:19]([O:26][CH2:27][C:28]([N:8]([CH3:9])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1)=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7483N-Methyl-4-nitroanilineHCID 8471TriethylamineHCID 177085Benzyloxyacetyl chloride

Product 1

HCID 66877507HCID 66877507, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-nitro-N-methylaniline in DCM (10 mL) was added at 0° C. was added Et3N (0.63 mL, 4.5 mmol) and 2-benzoxyacetyl chloride (0.513 mL, 3.3 mmol). After stirring for 15 h at room temperature, the reaction mixture was diluted with EtOAc, washed with Sat. NaHCO3, brine, dried and concentrated to give 2-benzoxy-N-methyl-N-(4-nitrophenyl)acetamide (0.63 g, 70%).

Workup

  1. additionwas added at 0° C.
  2. washwashed with Sat. NaHCO3, brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-07a9d99d7f8648a1a47f0c0e73049c35
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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