Hydrochloric Acid → HCID 69507061, compound

HRID 1623133Notes

Reaction equation

HRID 1623133 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][CH:18]=[O:19])[C:13]([CH2:20][CH2:21][CH3:22])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.[CH3:23][Mg]I.Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][CH:18]([OH:19])[CH3:23])[C:13]([CH2:20][CH2:21][CH3:22])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86052969HCID 86052969, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 69507061HCID 69507061, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(7-Bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde (2.77 g, 7.68 mmol) was dissolved in THF (75 mL), stirred at ambient temperature for 30 minutes, and cooled to 0° C. Methylmagnesium iodide (3.33 mL, 9.99 mmol, 3 M in diethyl ether) was added over 5 minutes. The reaction mixture was allowed to warm to ambient temperature. After 2 hours, 10% hydrochloric acid was added and the reaction mixture was concentrated under reduced pressure. The residue was neutralized with saturated aqueous sodium bicarbonate, extracted in 10% methanol in dichloromethane, dried over magnesium sulfate and concentrated under reduced pressure to provide 2.6 g of 5-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-ol as an orange-brown solid.

Workup

  1. temperaturecooled to 0° C
  2. temperatureto warm to ambient temperature
  3. waitAfter 2 hours
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. extractionextracted in 10% methanol in dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-771c02da5d57471dba6fc37668d952ba
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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