Dimethylformamide → HCID 68579328, compound

HRID 643294Notes

Reaction equation

HRID 643294 reaction equation
CN(C=O)C.[CH3:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[N:14][C:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[C:12]2O.O=S(Cl)[Cl:26]>>[Cl:26][C:12]1[C:11]2[C:16](=[C:7]([CH3:6])[CH:8]=[CH:9][CH:10]=2)[N:15]=[N:14][C:13]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178423897HCID 178423897, compound

Product 1

HCID 68579328HCID 68579328, compound

Procedure

Step 3: 2 Drops of DMF was added to a suspension of 8-methyl-3-phenylcinnolin-4-ol (60 mg) in SOCl2 (10 mL) and the reaction was refluxed for 0.5 hours. The reaction was concentrated, dilute with ethyl acetate and washed with water. The organic layer was dried over MgSO4 and concentrated to give crude 4-chloro-8-methyl-3-phenyl-cinnoline which was used for the next reaction without further purification. MS (ESI) m/z 255, 257;

Workup

  1. temperaturethe reaction was refluxed for 0.5 hours
  2. concentrationThe reaction was concentrated
  3. additiondilute with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-af361d8fbf06446484a249a757a9bf29
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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