Toluene → HCID 22646629, compound

HRID 393636Notes

Reaction equation

HRID 393636 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[NH:9][CH:8]=[CH:7][C:6]2=O.C1(C)C=CC=CC=1.S(Cl)([Cl:32])=O>CN(C=O)C>[ClH:32].[Cl:32][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 226466186-methoxy-7-[3-(1-pyrrolidyl)propyloxy]-4(1H)-quinolinone

Product 1

HCID 22646629HCID 22646629, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A solution of 6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)-1,4-dihydroquinolin-4-one (950 mg, 3.1 mmol) in thionyl chloride (25 ml) containing DMF (10 drops) was heated at reflux for 1.5 hours. After cooling, toluene was added and the volatiles were removed by evaporation. The residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinoline hydrochloride (1.23 g, 100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureAfter cooling
  4. customthe volatiles were removed by evaporation
  5. customThe residue was triturated with ether
  6. filtrationcollected by filtration
  7. washwashed with ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-a1c3a9ed46084622b5826ae5b564405e
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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