Formic Acid → 2-(N-formylaminomethyl)-4-(3-chloropropyl)pyridine

HRID 326143ノート

反応式

HRID 326143 の反応式
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][Cl:12])[CH:6]=[CH:5][N:4]=1.[OH-].[NH4+].[CH:15](O)=[O:16]>>[CH:15]([NH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][Cl:12])[CH:6]=[CH:5][N:4]=1)=[O:16]

参加物

4

反応物 3

HCID 284Formic AcidHCID 14923Ammonium HydroxideHCID 233218862-Aminomethyl-4-(3-chloropropyl)pyridine

生成物 1

HCID 233218752-(N-formylaminomethyl)-4-(3-chloropropyl)pyridine

実験手順

A solution of 2-aminomethyl-4-(3-chloropropyl)pyridine (0.47 g) in 1 ml of formic acid is heated at 90° for 18 hours, cooled to 0° and made basic by the addition of saturated ammonium hydroxide solution. Extraction with methylene chloride (4×10 ml), drying over sodium sulfate and evaporation yields 2-(N-formylaminomethyl)-4-(3-chloropropyl)pyridine (IR 1674 cm-1) which is heated at 90° in phosphorus oxychloride (0.75 g) for 15 hours. Excess phosphorus oxychloride is evaporated with toluene and the residue is suspended in methylene chloride (15 ml), cooled to 0° and made basic with saturated ammonium hydroxide. Extraction with methylene chloride (4×15 ml), drying over sodium sulfate and preparative thin layer chromatography (silica gel, EtOAc) of the residue yields 7-(3-chloropropyl)-imidazo[1,5-a]pyridine (Rf=0.24, EtOAc) as a gum; NMR (CDCl3) 3.58 (t, 2 H), 6.42 (q, 1 H), 7.21 (s, 1 H), 7.32 (s, 1 H), 7.88 (d, 1 H), 8.07 (s, 1 H).

後処理

  1. temperaturecooled to 0°
  2. extractionExtraction with methylene chloride (4×10 ml)
  3. dry with materialdrying over sodium sulfate and evaporation

出典と根拠

ORDレコード
ord-0ac94d29fe654402b7209b0b25aec079
出典データセット
uspto-grants-1984_04
特許番号
US04444775

反応ノート

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