Sodium Hydroxide → HCID 178469586, compound

HRID 402655Notes

Reaction equation

HRID 402655 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][CH2:11][C:12](=[O:19])[C:13]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:4]([CH3:20])[CH:3]=1.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][N:28]=2)[C:23]([CH:30]=O)=[CH:22]1.[OH-].[Na+]>C(O)C.Cl>[NH:21]1[C:29]2=[N:28][CH:27]=[CH:26][CH:25]=[C:24]2[C:23]([CH:30]=[C:11]2[O:10][C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][C:4]=3[CH3:20])=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12]2=[O:19])=[CH:22]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708344HCID 86708344, compound

Product 1

HCID 178469586HCID 178469586, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent3×

Procedure

To a solution of ethyl 2-[(4-hydroxy-2-methylphenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.10 g, 0.37 mmol) which similarly prepared according to the procedure described in the Example 74, Fourth step and 7-azaindole-3-carboxaldehyde (0.063 g, 0.43 mmol) in ethanol (2.5 mL), 2M hydrochloric acid in ethanol (0.46 mL, 0.92 mmol) was added at ambient temperature. The mixture was refluxed for 2.5 days. Cooled with ice bath, 2M sodium hydroxide solution (0.46 mL, 0.92 mmol) was added dropwise to neutralize, and ethanol (11 mL) was added and the mixture was refluxed for further 40 min. The precipitate was collected by filtration, washed with hot ethanol. The solid was washed with hexane then dried to afford the titled compound as solid (0.10 g, y. 70%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 2.5 days
  3. temperatureCooled with ice bath
  4. temperaturethe mixture was refluxed for further 40 min
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with hot ethanol
  7. washThe solid was washed with hexane
  8. customthen dried

Sources & evidence

ORD record
ord-1690d3373c304bf6adb73ec6e5d5aedf
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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