Dimethylformamide → 7-Benzyloxy-4-chloro-6-methoxycinnoline hydrochloride

HRID 2180120

Reaction equation

HRID 2180120 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](O)=[CH:14][N:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)([Cl:29])=O>>[ClH:29].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:29])=[CH:14][N:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178418820HCID 178418820, compound

Product 1

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

Procedure

The starting material, 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride, was obtained by heating a solution of 7-benzyloxy-4-hydroxy-6-methoxycinnoline (11 g, 39 mmol) in thionyl chloride (180 ml) containing DMF (1 ml) at reflux for 1 hour. After cooling, excess thionyl chloride was removed by evaporation and azeotroped with toluene. The residue was triturated with ether, filtered off, washed with ether and dried under vacuum to give 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride as a cream solid (13.6 g, quantitative).

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureAfter cooling
  3. customexcess thionyl chloride was removed by evaporation
  4. customazeotroped with toluene
  5. customThe residue was triturated with ether
  6. filtrationfiltered off
  7. washwashed with ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-2540037f84e64005ad031d59b25aee63
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Linked notes

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