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

HRID 1057326Notes

Reaction equation

HRID 1057326 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-5e20807965fb44c39946f8651bfce1d7
Source dataset
uspto-grants-2003_02
Patent number
US06514971B1

Reaction notes

Loading…