7-Benzyloxy-4-chloro-6-methoxycinnoline hydrochloride → 4-Chloro-7-hydroxy-6-methoxycinnoline

HRID 2180119

Reaction equation

HRID 2180119 reaction equation
Cl.C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[CH:15][N:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:20][C:14]1[C:13]2[C:18](=[CH:19][C:10]([OH:9])=[C:11]([O:21][CH3:22])[CH:12]=2)[N:17]=[N:16][CH:15]=1

Participants

3

Reactant 1

HCID 219910077-Benzyloxy-4-chloro-6-methoxycinnoline hydrochloride

Product 1

HCID 1357525234-Chloro-7-hydroxy-6-methoxycinnolineYield 94%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride (3.06 g, 9 mmol), in TFA (30 ml) was heated at reflux for 5 hours. After evaporation of the solvent, the residue was suspended in water and adjusted to pH7 with saturated aqueous sodium hydrogen carbonate solution. The resulting solid was filtered off, washed with water and ether and dried under vacuum to give 4-chloro-7-hydroxy-6-methoxycinnoline as a yellow solid (1.78 g, 94%).

Workup

  1. temperatureat reflux for 5 hours
  2. customAfter evaporation of the solvent
  3. filtrationThe resulting solid was filtered off
  4. washwashed with water and ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0ab58c77ede44c7db135dbd692d651d1
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Linked notes

Loading…