Hydrochloric Acid → 3-(Azidomethyl)-2-phenylquinoline-4-carboxylic acid

HRID 655910ノート

反応式

HRID 655910 の反応式
[N:1]([CH2:4][C:5]1[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([O:17]C)=[O:16])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+:2]=[N-:3].O.[OH-].[Li+].Cl>CO.O>[N:1]([CH2:4][C:5]1[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([OH:17])=[O:16])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+:2]=[N-:3]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57893572Methyl 3-(azidomethyl)-2-phenylquinoline-4-carboxylate

生成物 1

HCID 578935673-(Azidomethyl)-2-phenylquinoline-4-carboxylic acid収率 78.9%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of methyl 3-(azidomethyl)-2-phenylquinoline-4-carboxylate (2b) (1781 mg, 5.0 mmol) in methanol (50 mL) was added the solution of lithium hydroxide monohydrate (674 mg, 28.1 mmol) in 25 mL water. The reaction mixture was stirred at reflux for 4 h and the residue was acidified with 1 N HCl to pH 2. The volume of reaction mixture was reduced under reduced pressure. The resulting aqueous phase was extracted with ethyl acetate (150 mL). The organic phase was separated and washed with brine (20 ml) and dried over sodium sulfate and then concentrated in vacuo. Crystallization from ethyl acetate/hexane to afford the title compound (1200 mg, 66%) as an off white solid. MS APCI, m/z=305 (M+1). LCMS: 1.09 min.

後処理

  1. temperatureat reflux for 4 h
  2. customThe volume of reaction mixture
  3. extractionThe resulting aqueous phase was extracted with ethyl acetate (150 mL)
  4. customThe organic phase was separated
  5. washwashed with brine (20 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customCrystallization from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-42515479246a419e94e91f0bdb10180e
出典データセット
uspto-grants-2011_12
特許番号
US08071621B2

反応ノート

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