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Ethyl bromoacetate → Ethyl 2-((2-methoxyquinolin-8-yl)oxy)acetate

HRID 1429508
Notes
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Reaction equation

HRID 1429508 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([OH:13])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([O:13][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=[CH:8][CH:9]=2)[N:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 7627198-Quinolinol, 2-methoxy-

Product 1

HCID 90237870Ethyl 2-((2-methoxyquinolin-8-yl)oxy)acetateYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-methoxyquinolin-8-ol (500 mg, 2.86 mmol) in MeCN (10 mL) was added ethyl 2-bromoacetate (501 mg, 3.0 mmol) and K2CO3 (789 mg, 5.72 mmol). The mixture was stirred at 80° C. for 5 h. The mixture was filtered and the filtrate evaporated to give the desired compound (700 mg, yield 94%). LCMS (m/z): 262.1 [M+H]+

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-bd08b5ca9c5c48c5aab4c8172180954c
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08940726B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes