Aniline → N-Allylaniline

HRID 1490074Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8](Br)[CH:9]=[CH2:10].FC(F)(F)C(NC1C=CC=CC=1)=O>>[CH2:10]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]=[CH2:8]

Participants

Reactant 3

HCID 6115Aniline

HCID 7841Allyl bromide

HCID 678812,2,2-Trifluoro-N-phenylacetamide

Product 1

HCID 68525N-Allylaniline

Procedure

N-Allylaniline [NMR (200 MHz, DMSO-d6): δ 3.68 (t, J=5.2 Hz, 2H); 5.10 (d, J=10.2 Hz, 1H); 5.23 (d, J=17.2 Hz, 1H); 5.78 (br s, 1H); 5.75-5.97 (m, 1H); 6.52 (t, J=7.3 Hz, 2H); 6.56 (d, J=7.8 Hz, 2H); 7.06 (t, J=7.3 Hz, 2H)] was prepared from aniline and allyl bromide via trifluoroacetanilide using the general method described by Hodge (Harland, P. A.; Hodge, P; Maughan, W.; Wildsmith, E. Synthesis, 1984, 941).

Workup

customSynthesis, 1984, 941)

Sources & evidence

ORD record: ord-ee40bd9f533a4b4986277298ab3b568f
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05681830

Reaction notes

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