4-Methoxybenzylamine → HCID 67097724, compound

HRID 711668Notes

Reaction equation

HRID 711668 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([O:15][CH3:16])=[O:14].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4](=[O:12])[C:3]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 10657534Methyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 67097724HCID 67097724, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate (Example 69) (0.928 g, 3.91 mmol) was dissolved in DMF (6 mL), and 4-methoxybenzylamine (1.14 mL, 8.78 mmol) was added. The reaction was heated at 90° C. for 30 minutes, then cooled to room temperature and poured into a stirred mixture of 50 mL hexanes and 100 mL ice water. The resultant precipitate was collected by filtration and further chromatographed on silica gel (0% to 20% MeOH in dichloromethane) to give methyl 4-(4-methoxybenzylamino)-2-oxo-1,2-dihydroquinoline-3-carboxylate as an off white solid (0.841 g, 64%). MS 339 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resultant precipitate was collected by filtration
  3. customfurther chromatographed on silica gel (0% to 20% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-2ed14b0840f1451885e9c2c3b8f10c6d
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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