Aniline → 2-(Trifluoromethyl)quinoline

HRID 2215427Notes

Reaction equation

HRID 2215427 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5](=O)[C:6]([F:9])([F:8])[F:7].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCCl.C1(C)C(C)=CC=CC=1>[F:9][C:6]([F:7])([F:8])[C:5]1[CH:4]=[CH:3][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 9845Trifluoroacetic anhydrideHCID 2063589(3E)-4-(dimethylamino)-1,1,1-trifluorobut-3-en-2-one

Product 1

HCID 27778052-(Trifluoromethyl)quinoline

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 7237O-XyleneSolvent

Procedure

According to instructions in the literature (Baraznenok, I. L., Nenajdenko, V. G., Balenkova, E. S. Eur. J. Org. Chem. 1999, 937–941), 1.2 g (7.18 mmol) of (E)-4-(dimethylamino)-1,1,1-trifluoro-3-buten-2-one is reacted with 2.03 g (7.18 mmol) of trifluoroacetic acid anhydride and 1.30 ml (14.36 mmol) of aniline in 72 ml of 1,2-dichloroethane, then in 36 ml of xylene. After working-up and purification on silica gel with hexane-ethyl acetate (0–100%), 1.01 g (71% of theory) of the product is obtained.

Workup

  1. custompurification on silica gel with hexane-ethyl acetate (0–100%), 1.01 g (71% of theory) of the product
  2. customis obtained

Sources & evidence

ORD record
ord-91bcca3662d14d98a4d3c15fbda5f025
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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