Dimethylformamide → HCID 22566521, compound

HRID 25777Notes

Reaction equation

HRID 25777 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[CH:11]=2)[NH:6][C:5]([CH3:22])([CH3:21])[CH:4]=1.CN(C=O)C.[N-:28]=[N+:29]=[N-:30].[Na+]>CCOC(C)=O.O>[N:28]([CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[CH:11]=2)[NH:6][C:5]([CH3:22])([CH3:21])[CH:4]=1)=[N+:29]=[N-:30]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 225665354-(Bromomethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

Product 1

HCID 22566521HCID 22566521, compoundYield 156.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask equipped with a stir bar was added 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline (see Example 1) (0.36 mmol), DMF (3.6 mL), and NaN3 (0.54 mmol, 1.5 equiv). The reaction was stirred 48 hours under argon, then diluted with EtOAc and water, separated, and the aqueous phase was extracted with EtOAc. The combined organics were washed with water. The water was back-extracted with EtOAc and the combined organics were washed with brine and concentrated in vacuo. The residue was diluted with hexanes and a minimal amount of EtOAc and applied to a silica gel column. Flash chromatography, eluting with 0-30% EtOAc/hexanes provided 181 mg of 4-azidomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline as a brown oil.

Workup

  1. customTo a round bottom flask equipped with a stir bar
  2. customseparated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organics were washed with water
  5. extractionThe water was back-extracted with EtOAc
  6. washthe combined organics were washed with brine
  7. concentrationconcentrated in vacuo
  8. additionThe residue was diluted with hexanes
  9. washFlash chromatography, eluting with 0-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-a953b78637814013905e96e5affb86e9
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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