Hydrochloric Acid → HCID 67052300, compound

HRID 599454Notes

Reaction equation

HRID 599454 reaction equation
Cl.[CH3:2][CH:3]([CH3:27])[CH2:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[C:6]1[CH2:19][CH2:20][C:21]1([CH3:26])OCC[O:22]1.[OH-].[Na+]>O>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][CH2:20][C:21](=[O:22])[CH3:26])[N:5]([CH2:4][CH:3]([CH3:27])[CH3:2])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67052415HCID 67052415, compound

Product 1

HCID 67052300HCID 67052300, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (0.80 mL, 9.3 mmol) was added to a stirred suspension of 1-(2-methylpropyl)-2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (1.10 g, 3.10 mmol) in water (24 mL). A solution resulted and was stirred at room temperature for 30 minutes. The solution was adjusted to pH 12 with 20% aqueous sodium hydroxide. A white solid precipitated and was isolated by filtration, washed with water, and recrystallized from ethyl acetate to yield 0.6 g of 4-[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]butan-2-one as a monohydrate as a white powder, mp 172-174° C. 1H NMR (300 MHz, DMSO-d6) δ 7.98 (d, J=8.1 Hz, 1H), 7.61 (d, J=8.1 Hz, 1H), 7.41 (t, J=8.1 Hz, 1H), 7.26 (t, J=8.1 Hz, 1H), 6.41 (bs, 2H), 4.34 (d, J=7.5 Hz, 2H), 3.08 (bs, 41), 2.23 (s, 3H), 2.23-2.15 (m, 1H), 0.95 (d, J=6.9 Hz, 6H);

Workup

  1. customA solution resulted
  2. customA white solid precipitated
  3. customwas isolated by filtration
  4. washwashed with water
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-46fb5c5cb885420d9892175c5820cf8a
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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