Aniline → HCID 66913289, compound

HRID 2104519Notes

Reaction equation

HRID 2104519 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[C:21](O)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:25]1([NH:24][C:21]([C:8]2[CH:9]=[N:10][C:11]3[C:16]([C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]([F:18])([F:19])[F:20])=[O:22])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66913233HCID 66913233, compound

Product 1

HCID 66913289HCID 66913289, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-phenyl-8-trifluoromethyl-quinoline-3-carboxylic acid (0.24 g, 0.757 mmole) in 15 mL DMF was added aniline (0.137 mL, 1.51 mmole), EDCI-HCl (0.218 g, 1.13 mmole), and DMAP (0.184 g, 1.51 mmole). After stirring at room temperature overnight, the solution was partitioned between ethyl acetate and water and the aqueous layer was extracted with ethyl acetate. The combined organic phases were washed with water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded onto silica gel and chromatographed with hexanes:ethyl acetate (9:1) to afford 0.211 g (71%) of the title compound as a white solid: mp 207-208° C.; Calculated mass for C23H15N2F3O is 392.38, found by ESI MS, 393 (M+H)+, found by HRMS (ESI), 393.12056 (M+H)+; 1H NMR (DMSO-d6) δ 10.40 (bs, 1H), 9.25 (bs, 1H), 8.31 (d, 1H, J=6.9 Hz), 7.90 (d, 1H, J=8.3 Hz), 7.77 (t, 1H, J=7.5 Hz), 7.47 (m, 7H), 7.28 (t, 2H, J=7.5 Hz), 7.06 (t, 1H, J=7.06 Hz). Anal. Calcd for C23H15N2F3O: C, 70.40; H, 3.85; N, 7.14. Found: C, 70.00; H, 3.61; N, 6.96.

Workup

  1. customthe solution was partitioned between ethyl acetate and water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationThe organic phases were concentrated
  6. customchromatographed with hexanes:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-e6ff88bbf1a74dca93d609e699d0963b
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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