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Dimethyl Sulfate → N-[2-(4-Cyclohexylphenyl)4-methoxy-quinolin-6-yl]-acetamide

HRID 1394115
Notes
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Reaction equation

HRID 1394115 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:22]=[C:21]([OH:23])[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([NH:24][C:25](=[O:27])[CH3:26])[CH:19]=4)[N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(OC)(O[CH3:32])(=O)=O.CCCCCC>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH:22]=[C:21]([O:23][CH3:32])[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([NH:24][C:25](=[O:27])[CH3:26])[CH:19]=4)[N:14]=3)=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 8058HexaneHCID 178474047HCID 178474047, compound

Product 1

HCID 22643170N-[2-(4-Cyclohexylphenyl)4-methoxy-quinolin-6-yl]-acetamideYield 96.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Into a 500 mL three-neck round-bottom flask equipped with a condenser, magnetic stirrer and nitrogen inlet was added 35.7 g (0.099 moles) of N-[2-(4-cyclohexylphenyl)-4-hydroxy-quinolin-6-yl]-acetamide. The material was suspended in 250 mL of toluene with stirring and then 20.6 mL (0.21 moles) of dimethyl sulfate was added. The resulting suspension was heated with a silicone oil heating bath, to gentle a reflux for 18 hr. After this time the reaction was allowed to cool and hexane was added. The solids were collected by vacuum filtration and washed with hexane. After drying, the solids were suspended in a 2 L Erlenmeyer flask with 1 L of 5% sodium hydroxide solution. The vigorously stirred suspension was then heated to 70° C. for 30 min. This step converted the salt form of the material to the free base and removed some impurities. After cooling the solids were collected by vacuum filtration and then washed with water. The product was dried in a vacuum oven to give 35.8 g (96%) of a material which contained approximately 30% of side products, with the N-methylated material constituting the major impurity. This material was used in the following procedure without further purification.

Workup

  1. customInto a 500 mL three-neck round-bottom flask equipped with a condenser, magnetic stirrer and nitrogen inlet
  2. temperatureThe resulting suspension was heated with a silicone oil heating bath
  3. temperaturea reflux for 18 hr
  4. temperatureto cool
  5. filtrationThe solids were collected by vacuum filtration
  6. washwashed with hexane
  7. customAfter drying
  8. customremoved some impurities
  9. temperatureAfter cooling the solids
  10. filtrationwere collected by vacuum filtration
  11. washwashed with water
  12. customThe product was dried in a vacuum oven

Sources & evidence

ORD record
ord-2f1977b468c74a4e8831710addf4ebe4
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07348340B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes