Sodium hydride → HCID 43446516, compound

HRID 1922343Notes

Reaction equation

HRID 1922343 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].[H-].[Na+].[Cl:17][CH2:18][CH2:19][CH2:20]I>CN(C=O)C>[Cl:17][CH2:18][CH2:19][CH2:20][N:10]1[C:11]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 43446516HCID 43446516, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-nitro-3,4-dihydroquinolin-2(1H)-one (1.50 g, 7.81 mmol) was dissolved in anhydrous DMF (30 mL) in an argon purged round bottom flask. The reaction was stirred in an ice-water bath and 60% sodium hydride in mineral oil (1.25 g, 31.25 mmol) was added in one portion. The reaction became dark red-orange. This solution was transferred using a cannulating needle to a solution of 1-chloro-3-iodopropane (2.52 mL, 23.47 mmol) in DMF (20 mL). The reaction was stirred at room temperature for 5 hours. The reaction was quenched with brine (25 mL), transferred to a separatory funnel and partitioned with ethyl acetate (30 mL). The aqueous was extracted twice more with ethyl acetate (2×20 mL). The combined organic layers were washed with brine, dried with sodium sulphate, decanted and concentrated to afford a yellow solid. Purification by flash column chromatography afforded a yellow solid (Ethyl acetate:hexanes, 30:70-100:0); Yield: 1.58 g (75%).

Workup

  1. stirringThe reaction was stirred at room temperature for 5 hours
  2. customThe reaction was quenched with brine (25 mL)
  3. customtransferred to a separatory funnel
  4. custompartitioned with ethyl acetate (30 mL)
  5. extractionThe aqueous was extracted twice more with ethyl acetate (2×20 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried with sodium sulphate
  8. customdecanted
  9. concentrationconcentrated
  10. customto afford a yellow solid
  11. customPurification by flash column chromatography
  12. customafforded a yellow solid (Ethyl acetate:hexanes, 30:70-100:0)

Sources & evidence

ORD record
ord-fe911d40b1df40f5ba0dcc5c9044d0f7
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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