Dimethylformamide → HCID 22036992, compound

HRID 1789998Notes

Reaction equation

HRID 1789998 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.C([Li])CCC.CCCCCC.CN([CH:27]=[O:28])C.[NH4+].[Cl-]>O1CCCC1.C(OCC)C.C(O)C>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([CH:27]=[O:28])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 8058HexaneHCID 25517Ammonium Chloride2×HCID 47150308-Bromo-2-methylquinolineHCID 178418339Butyllithium

Product 1

HCID 22036992HCID 22036992, compoundYield 129.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

8-Bromo-2-methylquinoline (0.0675 mol) was added portionwise at −70° C. under N2 flow to a mixture of a solution of butyllithium in hexane (1.6M) (0.135 mol) in tetrahydrofuran (300 ml) and diethyl ether (300 ml). The mixture was stirred for 30 minutes. A solution of DMF (0.405 mol) in tetrahydrofuran (100 ml) was added quickly. The mixture was cooled to −70° C. and stirred for 15 minutes. Ethanol (70 ml) and a NH4Cl solution 10% were added. The mixture was brought to room temperature and stirred for 15 minutes. NH4Cl was added. The mixture was extracted with EtOAc. The organic layer was separated, washed with H2O, dried (MgSO4), filtered and the solvent was evaporated. The product was used without further purification, yielding 15 g (>100%) of 2-methyl-8-quinolinecarboxaldehyde (interm. 12).

Workup

  1. stirringstirred for 15 minutes
  2. customwas brought to room temperature
  3. stirringstirred for 15 minutes
  4. extractionThe mixture was extracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed with H2O
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe product was used without further purification

Sources & evidence

ORD record
ord-60ac4e1b4f544e8ba45a2727dbe686f7
Source dataset
uspto-grants-2006_07
Patent number
US07071192B1

Reaction notes

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