Acetaldehyde → HCID 57244807, compound

HRID 365513Notes

Reaction equation

HRID 365513 reaction equation
C(N1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)=[CH:11][CH:12]=2)[C:7]([CH3:27])([CH3:26])[CH2:6][CH2:5]1)(C)C.[CH:28](=O)[CH3:29].[C:31]([BH3-])#N.[Na+].[OH-].[Na+].[C:37](#[N:39])[CH3:38]>C(O)(=O)C>[CH:37]([N:39]1[C:9]2[C:8](=[CH:13][C:12]([CH2:11][CH2:10][NH:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=3)=[CH:28][CH:29]=2)[C:7]([CH3:26])([CH3:27])[CH2:6][CH2:5]1)([CH3:31])[CH3:38]

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 23291922HCID 23291922, compound2×

Product 1

HCID 57244807HCID 57244807, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amino]benzoate (Compound 8, 80 mg, 0.22 mmol) was dissolved in a 10% acetic acid in acetonitrile solution (2.0 mL). The solution was treated with acetaldehyde (0.10 mL, 1.80 mmol) and then sodium cyanoborohydride (18 mg, 0.29 mmol) and the reaction mixture was stirred at room temperature for 1.5 hours. 1M aqueous NaOH was added until pH=6 and the solution was extracted with ether (2×), washed with brine, and dried (Na2SO4). The filtered solution was concentrated under reduced pressure and the crude product was purified by silica gel chromatography (5% ethyl acetate in hexanes) to give the title compound (71 mg, 83%) as an oil.

Workup

  1. extractionthe solution was extracted with ether (2×)
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationThe filtered solution was concentrated under reduced pressure
  5. customthe crude product was purified by silica gel chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-cb5e434d2cf14d0a8f7e58fb321593bf
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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