Hydrogen Bromide → HCID 136367418, compound

HRID 913351Notes

Reaction equation

HRID 913351 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:21][C:20]([CH2:22][CH2:23][CH3:24])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1.Br.[OH-].[Na+]>C(O)(=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:21][C:20]([CH2:22][CH2:23][CH3:24])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 67392996HCID 67392996, compound

Product 1

HCID 136367418HCID 136367418, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To 7-benzyloxy-2-propylthiazolo[4,5-c]quinoline (prepared as described in Part F of Example 1, 4.52 g, 13.5 mmol) was added a 45 wt. % solution of hydrogen bromide in acetic acid (40 mL). The resulting solution was heated at 65° C. for 1.5 h, then cooled in an ice bath. Aqueous NaOH (50% w/w solution) was added slowly until the pH=7 and a light yellow solid formed. The solid was isolated by filtration, dried, and then suspended in boiling ethanol (25 mL) for 5 min. The mixture was allowed to cool to rt and a tan solid was isolated by filtration. The solid was washed with cold ethanol and dried in a vacuum oven to yield 7-hydroxy-2-propylthiazolo[4,5-c]quinoline (2.69 g, 82%).

Workup

  1. temperaturecooled in an ice bath
  2. customa light yellow solid formed
  3. customThe solid was isolated by filtration
  4. customdried
  5. customfor 5 min
  6. temperatureto cool to rt
  7. customa tan solid was isolated by filtration
  8. washThe solid was washed with cold ethanol
  9. customdried in a vacuum oven

Sources & evidence

ORD record
ord-86c787645f2248baaa098025af739f07
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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