Sodium hydride → HCID 14590305, compound

HRID 2309136Notes

Reaction equation

HRID 2309136 reaction equation
[H-].[Na+].Cl.[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15].[H][H].I[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>C1COCC1>[C:23]([O:22][C:20]([CH2:19][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH:5]([NH2:4])[C:6]1=[O:15])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 11021060Tert-butyl 2-iodoacetateHCID 134994283-Amino-3,4-dihydroquinolin-2(1H)-one--hydrogen chloride (1/1)HCID 178418361HCID 178418361, compound

Product 1

HCID 14590305HCID 14590305, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2.42 gm NaH (50% oil dispersion washed 3×hexanes) in 50 ml of THF at 0° C. was added solid 5 gm (0.025 mol) of 3-aminodihydrocarbostyrilhydrochloride (T. J. McCord, Arch. of Biochem. & Biophys. 102 48, 1963) and the mixture was stirred at 0° C. until the evolution of hydrogen had ceased. When the evolution stopped, the reaction mixture was warmed to room temperature and stirred an additional 1 hour, at which time a solution of 6 gm of t-butyl iodoacetate in 20 ml of THF was added dropwise. After an additional two hours of stirring at room temperature, the reaction was quenched with 20 ml of saturated NaHCO3, and the reaction mixture was diluted with 20 ml of H2O and extracted twice with 50 ml of 9:1 ethylacetate:acetonitrile. The organic layers were combined, filtered through MgSO4 and concentrated in vacuo to give 5 gm of 1-t-butoxycarbonylmethyl-3 -aminodihydrocarbostyril.

Workup

  1. additionwas added dropwise
  2. customthe reaction was quenched with 20 ml of saturated NaHCO3
  3. additionthe reaction mixture was diluted with 20 ml of H2O
  4. extractionextracted twice with 50 ml of 9:1 ethylacetate
  5. filtrationfiltered through MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90fa7445650747d6b4b694ad2d4b8e90
Source dataset
uspto-grants-1987_09
Patent number
US04692522

Reaction notes

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