Sodium hydride → HCID 136342844, compound

HRID 415525Notes

Reaction equation

HRID 415525 reaction equation
[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([NH2:19])[N:14]([CH2:15][CH2:16][CH2:17]Cl)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[H-].[Na+]>CN(C)C(=O)C>[Cl:1][C:2]1[C:11]2[N:12]=[C:13]3[NH:19][CH2:17][CH2:16][CH2:15][N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86633738HCID 86633738, compound

Product 1

HCID 136342844HCID 136342844, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a round-bottomed flask containing 4-chloro-1-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-2-amine (7.92 g, 26.8 mmol) was added N,N-dimethylacetamide (200 mL) and the mixture was stirred for 5 minutes. To the stirred solution was added sodium hydride (60% dispersion in mineral oil, 3.9 g, 80.54 mmol) and the reaction was stirred at 50° C. After 1.5 h the reaction was cooled to ambient and quenched by the careful addition of water (1 L). The reaction was transferred to a separatory funnel and ethyl acetate (1 L) was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (1 L). The organic layers were combined, washed with water (2×1 L), dried (MgSO4), filtered, and the solvent was evaporated. The resultant product was dried under reduced pressure to afford 6-chloro-8,9,10,11-tetrahydropyrimido[1′,2′:1,2]imidazo[4,5-c]quinoline (6.54 g).

Workup

  1. stirringthe reaction was stirred at 50° C
  2. temperatureAfter 1.5 h the reaction was cooled to ambient and
  3. customquenched by the careful addition of water (1 L)
  4. customThe reaction was transferred to a separatory funnel
  5. additionethyl acetate (1 L) was added
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate (1 L)
  8. washwashed with water (2×1 L)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customthe solvent was evaporated
  12. dry with materialThe resultant product was dried under reduced pressure

Sources & evidence

ORD record
ord-ef10dc9d283d4975a807aeb9e877ccf3
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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