1,2-Dichlorobenzene → HCID 86754320, compound

HRID 583400Notes

Reaction equation

HRID 583400 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH:5]=[CH:6][CH:7]([N:16]([CH3:33])[C:17](=[O:32])[C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[CH3:2].ClC1C=CC=CC=1Cl>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][CH:7]([N:16]([CH3:33])[C:17](=[O:32])[C:18]1[CH:19]=[C:20]([C:28]([F:30])([F:29])[F:31])[CH:21]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:23]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 53721008HCID 53721008, compound

Product 1

HCID 86754320HCID 86754320, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 29 g of 4-[N'-methyl-N'-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(4-chlorophenyl)-pent-2-enoic acid ethyl ester [see example 2b)] in 300 ml of tetrahydrofuran is hydrogenated for 0.5 hour in the presence of 3 g of palladium/activated carbon (10%) and 6 g of 1,2-dichlorobenzene. The reaction mixture is then filtered and concentrated by evaporation. The residue is chromatographed (silica gel, hexane/ethyl acetate 3:1). In this way the title compound is obtained in the form of a colourless oil. 1H-NMR, 500 MHz, DMSO, 140°, delta (ppm): 7.99(s, 1H), 7.51(s, 2H), 7.30(td, 2H), 7.18(d, 2H), 4.5(b, 1H), 4.06(q, 2H), 2.9(m, 1H), 2.8(m, 4H), 2.35(m, 2H), 2.02(m, 1H), 1.90(m, 1H), 1.19(t, 3H).

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated by evaporation
  3. customThe residue is chromatographed (silica gel, hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-ed6f2e3bff8e47c4a2dfd8ada65cdecb
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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