3-Bromoquinoline → 3-(Dimethoxyacetyl)quinoline

HRID 34745

Reaction equation

HRID 34745 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([Li])CCC.[CH3:17][O:18][CH:19]([O:28][CH3:29])[C:20](N1CCOCC1)=[O:21]>C1COCC1>[CH3:17][O:18][CH:19]([O:28][CH3:29])[C:20]([C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:21]

Participants

5

Reactant 3

HCID 214133-BromoquinolineHCID 21298597N-(dimethoxyacetyl)morpholineHCID 178418339Butyllithium

Product 1

HCID 142769343-(Dimethoxyacetyl)quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Bromoquinoline (3.29 ml., 0.032 mol) was dissolved in 300 ml. THF and cooled to -78°. n-Butyllithium (13.6 ml. of 2.5M in hexane, 0.034 ml.) was added slowly and the mixture stirred 15 minutes at -75° to -78°. N-(Dimethoxyacetyl)morpholine (5.98 g., 0.032 mol) in 10 ml. THF was then added and stirring continued for 1.75 hours at the same temperature. The reaction was then quenched into 300 ml. saturated NH4Cl. The aqueous layer was separated and extracted 4×100 ml. ether. The organic layers were combined, dried over MgSO4, stripped to yield title product, 7.0 g., bp 120°-123°/0.125 torr.

Workup

  1. stirringstirring
  2. waitcontinued for 1.75 hours at the same temperature
  3. customThe reaction was then quenched into 300 ml
  4. customThe aqueous layer was separated
  5. extractionextracted 4×100 ml
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-97c01dee82af4b81ba08bf372d90172a
Source dataset
uspto-grants-1988_08
Patent number
US04762921

Linked notes

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