Hydrochloric Acid → HCID 86718150, compound

HRID 2205168Notes

Reaction equation

HRID 2205168 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6](/[CH:7]=[N:8]/[C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.[C:21]1([CH2:27][CH:28]=O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>O1CCCC1.CS(C)=O>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]2[C:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:28][C:18]3[C:9](=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=3)[N:8]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 998PhenylacetaldehydeHCID 178497921HCID 178497921, compound

Product 1

HCID 86718150HCID 86718150, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (E)-methyl 3-(4-methoxybenzylideneamino)benzoate (1.1 g, 4.08 mmol, 1.00 equiv), 2-phenylacetaldehyde (480 mg, 4.00 mmol, 1.00 equiv), hydrochloric acid in tetrahydrofuran (0.5 mL, 10M) and DMSO (2 mL) was placed in a 10-mL sealed tube and stirred overnight at 70° C. in an oil bath. The resulting mixture was concentrated under vacuum and purified via Flash-Prep-HPLC (H2O/CH3CN=10% increasing to H2O/CH3CN=60% within 5 min; Detector, UV 254 nm) affording 70 mg (5%) of methyl 2-(4-methoxyphenyl)-3-phenylquinoline-7-carboxylate as a yellow solid.

Workup

  1. customsealed tube
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. custompurified via Flash-Prep-HPLC (H2O/CH3CN=10% increasing to H2O/CH3CN=60% within 5 min; Detector, UV 254 nm)

Sources & evidence

ORD record
ord-e7e78598b8214aa4a3a0cec8977ed620
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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