3-Bromoquinoline → 3-(Dimethoxyacetyl)quinoline

HRID 653045Notes

Reaction equation

HRID 653045 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 MgSO4O, 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 MgSO4O

Sources & evidence

ORD record
ord-08b32b1bda01412ca4af4d79f02e593d
Source dataset
uspto-grants-1987_06
Patent number
US04675186

Reaction notes

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