Hydrogen Bromide → 6-Hydroxy-3-aminoquinoline di-hydrobromide

HRID 495472Notes

Reaction equation

HRID 495472 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=2)[CH:11]=[C:10]([NH2:20])[CH2:9]1)=O)(C)(C)C.[BrH:21]>>[BrH:21].[BrH:21].[OH:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:8]=[CH:9][C:10]([NH2:20])=[CH:11]2

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 22326880N-tert-butyloxycarbonyl-6-methoxy-3-aminoquinoline

Product 1

HCID 223268146-Hydroxy-3-aminoquinoline di-hydrobromide

Conditions

Temperature
0 °C

Procedure

A stirred suspension of N-tert-butyloxycarbonyl-6-methoxy-3-aminoquinoline (Example 134, Step F) (0.274 g, 1 mmol) in HBr (48%, 2.5 mL) was heated at reflux for 48 h. The reaction was cooled to 0° C., and the yellow crystalline solid was filtered off and washed with a small amount of ice-cold water followed by acetone. The yellow crystalline solid was dried over P2O5 to give 6-hydroxy-3-aminoquinoline di-hydrobromide.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 h
  3. filtrationthe yellow crystalline solid was filtered off
  4. washwashed with a small amount of ice-cold water
  5. dry with materialThe yellow crystalline solid was dried over P2O5

Sources & evidence

ORD record
ord-cc5f1e8a933e4fe790c1f7d7e7729453
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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