1,1-Bis(propan-2-yl) 3,3-dimethoxycyclobutane-1,1-dicarboxylate → 7-Chloro-2-phenyl4-trifluoromethyl-quinoline

HRID 1028832Notes

Reaction equation

HRID 1028832 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][CH:7]=1.C(OC(C1(C(OC(C)C)=O)CC(OC)(OC)C1)=O)(C)C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:8]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 49133591,1-Bis(propan-2-yl) 3,3-dimethoxycyclobutane-1,1-dicarboxylateHCID 666768124-(3-Chloro-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one

Product 1

HCID 146176127-Chloro-2-phenyl4-trifluoromethyl-quinoline

Procedure

4-(3-Chloro-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one (2.8 g, 0.0086 mole) and polyphosphoric acid (60 mL) in a 250 mL 3 neck round bottom flask was stirred mechanically under an atmosphere of Nitrogen at 165° C. internal temperature for 3 h. The reaction was poured over stirring ice water (600 ml). The product precipitated, and was collected by suction filtration, washed with water, and air dried overnight. The solids remaining in the Buchner funnel, and beaker from aqueous quench were rinsed into a flask concentrated in vacuo, then combined with the filtered sample and chromatographed on silica gel with 3:1 Hexanes/methylene chloride to afford the title compound as a white solid; 1H NMR (CDCl3, 400 MHz) δ 7.53-7.59 (m, 3H), 7.60-7.63 (dd, 1H, J=2.2 & J=9.1 Hz), 8.06-8.09 (dq, 1H, J=1.9 & J=9.0 Hz), 8.16-8.20 (m, 3H), 8.29 (d, 1H, J=2.1 Hz); 19F NMR δ −61.48; MS (ES+): 308.0 (100) [MH+], 310.0 (30) [M+2H+].

Workup

  1. additionThe reaction was poured
  2. customThe product precipitated
  3. filtrationwas collected by suction filtration
  4. washwashed with water, and air
  5. customdried overnight
  6. customfrom aqueous quench
  7. washwere rinsed into a flask
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica gel with 3:1 Hexanes/methylene chloride

Sources & evidence

ORD record
ord-d5ce361fc3db46808274ada6d22a4d9a
Source dataset
uspto-grants-2014_05
Patent number
US08735405B2

Reaction notes

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