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Sodium ethoxide → ethyl 3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968016
Notes
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Reaction equation

HRID 1968016 reaction equation
[CH:1](=[N:8]/[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][O:12][C:13]2=[O:18])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][N:20]1[C:24]([CH:25]=O)=[N:23][CH:22]=[N:21]1.[CH3:27][CH2:28][O-:29].[Na+]>C(OCC)(=O)CC>[CH3:19][N:20]1[C:24]([CH:25]2[C:28](=[O:29])[C:27]3[C:14]([C:13]([O:12][CH2:11][CH3:10])=[O:18])=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][CH:1]2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:23][CH:22]=[N:21]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 136242781-methyl-1H-1,2,4-triazole-5-carbaldehydeHCID 178519069HCID 178519069, compound

Product 1

HCID 67258123ethyl 3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 14.2%

Reagents, catalysts & solvents 1

HCID 7749Ethyl Propionate
Solvent

Conditions

Temperature
41 °C

Procedure

To a solution of (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (1.78 g, 7.5 mmol) and 1-methyl-1H-1,2,4-triazole-5-carbaldehyde (1.01 g, 9.16 mmol) in ethyl propionate (110 mL) was added EtONa (sodium (490 mg, 21 mmol) in 35 mL ethanol) at 40° C., then the mixture was stirred at 41° C. for 3 hr. The resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (150 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, dichloromethane: methanol=200:1 to 50:1) to obtain a green solid (400 mg, yield 14%). LC-MS (ESI) m/z: 377 (M+1)+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (150 mL×4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, dichloromethane: methanol=200:1 to 50:1)

Sources & evidence

ORD record
ord-a4923f3f994042e995a77962c277bcb9
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08420650B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes