Hydrochloric Acid → HCID 57458160, compound

HRID 1924794Notes

Reaction equation

HRID 1924794 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=C(C#N)[CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[OH-:17].[Na+].Cl.[CH3:20][CH2:21][OH:22]>O>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:20]([C:21]([OH:17])=[O:22])[CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 57458161HCID 57458161, compound

Product 1

HCID 57458160HCID 57458160, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6-tert-butylquinoline-2-carbonitrile (295 mg, 1.40 mmol) and 2M-aqueous sodium hydroxide (3 ml) in EtOH (4.5 ml) was stirred for 4 hours at reflux. The mixture was diluted with water (10 ml), neutralized by 2M-aqueous hydrochloride and extracted with EtOAc (30 ml). The organic layer was dried over sodium sulfate, filtrated, and concentrated in vacuo to furnish the title compound (313 mg, quant.) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.40 (9H, s), 7.93-7.97 (2H, m), 8.01-8.11 (2H, m), 8.41 (1H, d, J=8.1 Hz) MS (ESI): m/z 230 (M+H)+.

Workup

  1. temperatureat reflux
  2. extractionextracted with EtOAc (30 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9c15d6ea3c54d1795b743658621d187
Source dataset
uspto-grants-2012_05
Patent number
US08178558B2

Reaction notes

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