Ethanolamine → Aziridin-1-yl(3-methoxy-4-nitrophenyl)methanone

HRID 1487621Notes

Reaction equation

HRID 1487621 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([OH:8])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br.[NH2:39][CH2:40][CH2:41]O>C1(C)C=CC=CC=1>[N:39]1([C:6]([C:5]2[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:8])[CH2:41][CH2:40]1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 787643-Methoxy-4-nitrobenzoic acid

Product 1

HCID 86726450Aziridin-1-yl(3-methoxy-4-nitrophenyl)methanoneYield 34%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methoxy-4-nitrobenzoic acid (1 equiv) in toluene (0.21 M) was added triphenyl phosphine (1.5 equiv), carbon tetrabromide (1.6 equiv), TEA (2 equiv) and 2-aminoethanol (0.7 equiv). Then the resulting mixture was stirred at 80° C. for 1 h. The reaction mixture was filtered, the filtrate was concentrated and the crude was purified by reverse phase HPLC (10%-95% acetonitrile in water) to give the title compound (34% yield) as a yellow solid. MS (ESI) m/z 223.1 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe crude was purified by reverse phase HPLC (10%-95% acetonitrile in water)

Sources & evidence

ORD record
ord-40eccb94854a4207a6d508678f09034c
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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