Dimethylformamide → HCID 86629136, compound

HRID 1949031Notes

Reaction equation

HRID 1949031 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[CH:6]=[CH:5]2.C([Li])CCC.CN(C)[CH:29]=[O:30]>O1CCCC1>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:29]=[O:30])[CH:3]=2)[N:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 68574436HCID 68574436, compoundHCID 178418339Butyllithium

Product 1

HCID 86629136HCID 86629136, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

(6-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (2.0 g, 5.83 mmol) was dissolved in 100 mL tetrahydrofurane. n-Butyllithium solution (1.6 M in hexane, 9.1 mL, 14.6 mmol) was slowly added at −78° C. The reaction mixture was allowed to warm to −10° C. and stirred at this temperature for 45 min. The reaction mixture was then cooled again to −78° C. and dimethylformamide (1.07 g, 14.6 mmol) was added. The mixture was then slowly warmed up and quenched with 200 mL water at 5° C. The solvent was evaporated off. The residue was extracted three times with ethyl acetate (200 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient). 2-(2-Methoxy-benzylamino)-quinoline-6-carbaldehyde was obtained as a light yellow solid (683 mg, 40%), MS: m/e=293.1 (M+H+).

Workup

  1. temperatureThe reaction mixture was then cooled again to −78° C.
  2. temperatureThe mixture was then slowly warmed up
  3. customquenched with 200 mL water at 5° C
  4. customThe solvent was evaporated off
  5. extractionThe residue was extracted three times with ethyl acetate (200 mL each)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient)

Sources & evidence

ORD record
ord-5836be87cd504dc0bd848d9f936a2e01
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

Loading…