Thionyl Chloride → (4-Chloro-7-methoxyquinolin-6-yl)carbamic acid benzyl ester

HRID 1433519Notes

Reaction equation

HRID 1433519 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[NH:17][CH:16]=[CH:15][C:14]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:27])=O>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2[Cl:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58931364(7-Methoxy-4-oxo-1,4-dihydroquinolin-6-yl)carbamic acid benzyl ester

Product 1

HCID 58931435(4-Chloro-7-methoxyquinolin-6-yl)carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(7-Methoxy-4-oxo-1,4-dihydroquinolin-6-yl)carbamic acid benzyl ester (2 g) was added to a mixture of thionyl chloride (20 ml) and N,N-dimethylformamide (0.5 ml), and the mixture was heated to reflux for 2 hours. After completion of the reaction, the thionyl chloride was distilled off, and a procedure of toluene addition and concentration was repeated 3 times to obtain the title compound (2.4 g) as a solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customAfter completion of the reaction
  4. distillationthe thionyl chloride was distilled off
  5. additiona procedure of toluene addition and concentration

Sources & evidence

ORD record
ord-d2cb6a523204432a8cf73bfcb3b6e46f
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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