Sodium hydride → HCID 14590305, compound

HRID 2351273Notes

Reaction equation

HRID 2351273 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)) stirring at 0° C. until the evolution of hydrogen had ceased at which time the reaction mixture was warmed to room temperature and stirred a further 1 hour. To the stirred reaction mixture was added dropwise a solution of 6 gm of t-butyl iodoacetate in 20 ml of THF stirring a further 2 hours at room temperature at which time the reaction was quenched with 20 ml of saturated NaHCO3. The reaction mixture was diluted with 20 ml of H2O and extracted 2×50 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. NMR (CDCl3, TMS) 1.4 (s, 9H); 2.0-3.2 (m, 4H), 3.4-3.8 (m, 1H); 4.6 (Q, 2H); 6.6-7.2 (m, 4H) IR C=O 1738, 1680

Workup

  1. customTo the stirred reaction mixture
  2. customwas quenched with 20 ml of saturated NaHCO3
  3. additionThe reaction mixture was diluted with 20 ml of H2O
  4. extractionextracted 2×50 ml of 9:1 ethylacetate
  5. filtrationfiltered through MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04b91d86fa35413c918e04491335a606
Source dataset
uspto-grants-1989_10
Patent number
US04873235

Reaction notes

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