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Dichloromethane → 3-Acetoxy-8-methoxy quinoline

HRID 399746
Notes
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Reaction equation

HRID 399746 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[O:12][CH3:13].C(N(CC)CC)C.ClCCl.[C:24](Cl)(=[O:26])[CH3:25]>O>[C:24]([O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[O:12][CH3:13])(=[O:26])[CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 110843893-Quinolinol, 8-methoxy-2×

Product 1

HCID 189450663-Acetoxy-8-methoxy quinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

175 mg of 3-hydroxy-8-methoxy quinoline [compound (V)] prepared in example 6 and 132 mg of triethyl amine were added to 10 ml of dichloromethane. After cooled to 0° C., 0.1 ml of acetyl chloride was slowly added dropwise. The solution was agitated for 1 hour, and water was added to the solution. The solution was extracted with dichloromethane and washed with water. The dichloromethane layer was dried with anhydrous magnesium sulfate. The dichloromethane was removed by vacuum distillation to give 195 mg of 3-acetoxy-8-methoxy quinoline as an oil.

Workup

  1. extractionThe solution was extracted with dichloromethane
  2. washwashed with water
  3. dry with materialThe dichloromethane layer was dried with anhydrous magnesium sulfate
  4. customThe dichloromethane was removed by vacuum distillation

Sources & evidence

ORD record
ord-39fa172cb72648fe9375f59f6e330b81
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05824689

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes