Sodium Hydroxide → HCID 67156407, compound

HRID 1035515Notes

Reaction equation

HRID 1035515 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH:15]([CH3:19])[CH2:16][CH2:17][OH:18])[C:13]([CH2:20]O)=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.[OH-].[Na+]>Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[N:14]4[CH:15]([CH3:19])[CH2:16][CH2:17][O:18][CH2:20][C:13]4=[N:12][C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67156788HCID 67156788, compound

Product 1

HCID 67156407HCID 67156407, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 3-[7-bromo-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butan-1-ol (3.27 g, 9.34 mmol) in concentrated hydrochloric acid (35 mL) was stirred and heated at 120° C. for three hours and then poured into ice-cold deionized water (80 mL). Aqueous sodium hydroxide (50% w/w) was added to adjust the solution to pH 7, and a precipitate formed. The mixture was extracted with dichloromethane, and the dichloromethane was removed under reduced pressure. The solid residue was triturated with diethyl ether and isolated by filtration to provide 2.62 g of 3-bromo-12-methyl-11,12-dihydro-8H,10H-[1,4]oxazepino[4′,3′:1,2]imidazo[4,5-c]quinoline.

Workup

  1. customa precipitate formed
  2. extractionThe mixture was extracted with dichloromethane
  3. customthe dichloromethane was removed under reduced pressure
  4. customThe solid residue was triturated with diethyl ether
  5. customisolated by filtration

Sources & evidence

ORD record
ord-cd3c4375fc1e46d89f442f2e6581d819
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

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