Ethanol → HCID 178517225, compound

HRID 928822Notes

Reaction equation

HRID 928822 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[CH:6]=[C:5]2[OH:13].CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O.[F:32][C:33]([F:43])([F:42])[C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1.C(O)C>N1C=CC=CC=1>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[C:6]([CH2:38][C:37]1[CH:36]=[CH:35][C:34]([C:33]([F:32])([F:42])[F:43])=[CH:41][CH:40]=1)=[C:5]2[OH:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 679964-(Trifluoromethyl)benzaldehydeHCID 70849Hantzsch esterHCID 178516557HCID 178516557, compound

Product 1

HCID 178517225HCID 178517225, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
105 °C

Procedure

To a suspension of 6-iodoquinoline-2,4-diol (498.2 g, 1.736 mol) and diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (439.6 g, 1.736 mol) in pyridine (3.5 L) was added 4-(trifluoromethyl)benzaldehyde (332.4 g, 1.909 mol). The resulting mixture was warmed with stirring to 105° C. for a period of 6 h. After cooling to room temperature, the heterogeneous mixture was treated with ethanol (4.6 L). White solids were isolated through filtration, washed with 57:43 ethanol:pyridine (800 mL), and dried in a vacuum oven at 65° C. The title compound was obtained in a 1:0.92 ratio with pyridine and used directly in the subsequent step.

Workup

  1. temperatureThe resulting mixture was warmed
  2. temperatureAfter cooling to room temperature
  3. customWhite solids were isolated through filtration
  4. washwashed with 57:43 ethanol
  5. dry with materialpyridine (800 mL), and dried in a vacuum oven at 65° C

Sources & evidence

ORD record
ord-bb53fb672dff4e6499a401707ddb783d
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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