Lithium hydroxide, monohydrate → HCID 67156788, compound

HRID 221555Notes

Reaction equation

HRID 221555 reaction equation
O.[OH-].[Li+].C([O:7][CH2:8][CH2:9][CH:10]([N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][C:20]([Br:25])=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:14]=[C:13]1[CH2:26][O:27]C(=O)C)[CH3:11])(=O)C>CO>[Br:25][C:20]1[CH:21]=[CH:22][C:23]2[C:24]3[N:12]([CH:10]([CH3:11])[CH2:9][CH2:8][OH:7])[C:13]([CH2:26][OH:27])=[N:14][C:15]=3[CH:16]=[N:17][C:18]=2[CH:19]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67157355HCID 67157355, compound

Product 1

HCID 67156788HCID 67156788, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium hydroxide hydrate (5.3 g, 126 mmol) was added to a solution of 3-{2-[(acetyloxy)methyl]-7-bromo-1H-imidazo[4,5-c]quinolin-1-yl}butyl acetate (9.14 g, 21.0 mmol) in methanol (150 mL). The resulting mixture was stirred for two days at room temperature and filtered. The methanol was removed from the filtrate under reduced pressure. The crude product mixture was partitioned between dichloromethane and 10% aqueous sodium carbonate. The aqueous fraction was extracted with dichloromethane, and the combined organic fractions were concentrated under reduced pressure. The resulting solid was triturated with acetonitrile, isolated by filtration, and washed with cold acetonitrile to provide 2.13 g of 3-[7-bromo-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butan-1-ol. A portion of this material was mixed with material from a separate run.

Workup

  1. filtrationfiltered
  2. customThe methanol was removed from the filtrate under reduced pressure
  3. customThe crude product mixture was partitioned between dichloromethane and 10% aqueous sodium carbonate
  4. extractionThe aqueous fraction was extracted with dichloromethane
  5. concentrationthe combined organic fractions were concentrated under reduced pressure
  6. customThe resulting solid was triturated with acetonitrile
  7. customisolated by filtration
  8. washwashed with cold acetonitrile

Sources & evidence

ORD record
ord-c2e81e2deb6b4987ab77be25f9b84905
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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