4-Nitrophenethylamine → HCID 59128265, compound

HRID 1990976Notes

Reaction equation

HRID 1990976 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:14][O:15][CH:16]=[O:17]>C(Cl)Cl.CO>[CH3:14][O:15][C:16](=[O:17])[NH:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 951534-NitrophenethylamineHCID 17803410Chloromethyl formate

Product 1

HCID 59128265HCID 59128265, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [2-(4-nitrophenyl)ethyl]amine (6.06 g, 30 mmol) in CH2Cl2 (75 ml), MeOH (5 ml), and TEA (9.5 ml) at 0° C. was added chloromethylformate (3.39 g, 36 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 hour concentrated in vacuo, and partitioned between ethyl acetate and water, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford a yellow solid (6.6 g, 98%). Mp: 38° C., MS (ES−): 223 (M−H).

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water (50 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33d8c4f49c114a9bbfc620fbe6138b21
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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