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

HRID 422736Notes

Reaction equation

HRID 422736 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-3a1ffd14cf19489abe79a364c06dfeb1
Source dataset
uspto-grants-2012_01
Patent number
US08101613B2

Reaction notes

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