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

HRID 1057332Notes

Reaction equation

HRID 1057332 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

The starting material, 4-chloro-7-hydroxy-6-methoxycinnoline was obtained by heating a solution of 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride (3.06 g, 9 mmol), (prepared as described for the starting material in Example 6), in TFA (30 ml) 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. custom(prepared
  2. temperatureat reflux for 5 hours
  3. customAfter evaporation of the solvent
  4. filtrationThe resulting solid was filtered off
  5. washwashed with water and ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7a2a5ada340e43df8378062cf1a3e475
Source dataset
uspto-grants-2003_02
Patent number
US06514971B1

Reaction notes

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