Hydrochloric Acid → HCID 67052308, compound

HRID 599456Notes

Reaction equation

HRID 599456 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:21][CH2:22][C:23]3([CH3:28])OCC[O:24]3)[N:15]([CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1.[OH-].[Na+].ClCCl>O>[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:21][CH2:22][C:23](=[O:24])[CH3:28])[N:15]([CH2:16][C:17]([OH:19])([CH3:18])[CH3:20])[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67052434HCID 67052434, compound

Product 1

HCID 67052308HCID 67052308, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (0.20 mL, 2.4 mmol) was added to a stirred suspension of 1-{4-amino-2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol (0.30 g, 0.81 mmol) in water (5 mL). A solution resulted and was stirred at room temperature for 3 hours. The solution was adjusted to pH 13 with 20% aqueous sodium hydroxide. A gummy solid formed. Dichloromethane was added, but the solid did not dissolved. The mixture was poured into a separatory funnel, then the contents of the funnel were filtered. The white solid isolated by filtration was washed with water and dried to yield 0.17 g of 4-[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]butan-2-one as a white powder, mp 181-184° C.

Workup

  1. customA solution resulted
  2. customA gummy solid formed
  3. dissolutionthe solid did not dissolved
  4. additionThe mixture was poured into a separatory funnel
  5. filtrationthe contents of the funnel were filtered
  6. customThe white solid isolated by filtration
  7. washwas washed with water
  8. customdried

Sources & evidence

ORD record
ord-fb1336d6cce942e2b083c72cee7640f8
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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