1,1-Dichloroethane → 3-Azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide

HRID 1887793ノート

反応式

HRID 1887793 の反応式
[CH3:1][N:2]([CH3:24])[C:3]([C:5]1[N:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH3:15])=[CH:11][CH:10]=[C:9]([Cl:17])[CH:8]=2)=[O:4].BrN1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.ClC(Cl)C.[N-:49]=[N+:50]=[N-:51].[Na+]>>[CH3:24][N:2]([CH3:1])[C:3]([C:5]1[N:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH2:15][N:49]=[N+:50]=[N-:51])=[CH:11][CH:10]=[C:9]([Cl:17])[CH:8]=2)=[O:4]

参加物

6

反応物 5

HCID 63651,1-DichloroethaneHCID 6547AzobisisobutyronitrileHCID 33557Sodium AzideHCID 67184N-bromobutanimideHCID 712089157-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide

生成物 1

HCID 712090383-Azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide収率 43.1%

実験手順

In a 50 mL round bottom flask, 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide (0.54 g, 1.58 mmol), N-bromosuccinimide (0.367 g, 2.06 mmol) and AIBN (78 mg, 0.475 mmol) were added to dichloroethane (6.0 mL). The reaction mixture was heated to reflux for 5 hr. The mixture was concentrated to dryness and the crude (containing 3-bromomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide) was redissolved in DMF (6.0 mL). To the reaction mixture was added sodium azide (0.515 g, 7.92 mmol). The reaction was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate and water and the organic layer was washed with aqueous sodium bicarbonate solution. The organic layer was dried, evaporated to dryness and purified by flash chromatography using 40% ethyl acetate-hexane to afford 3-azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide (260 mg, 43% yield).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hr
  3. concentrationThe mixture was concentrated to dryness
  4. additionthe crude (containing 3-bromomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide)
  5. dissolutionwas redissolved in DMF (6.0 mL)
  6. customThe mixture was partitioned between ethyl acetate and water
  7. washthe organic layer was washed with aqueous sodium bicarbonate solution
  8. customThe organic layer was dried
  9. customevaporated to dryness
  10. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-927c0d178852409b94eaaae9706ca1df
出典データセット
uspto-grants-2013_08
特許番号
US08501732B2

反応ノート

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