Morpholine → Propan-2-yl 6-(morpholin-4-yl)pyridine-3-carboxylate

HRID 746510ノート

反応式

HRID 746510 の反応式
Cl[C:2]1[CH:13]=[CH:12][C:5]([C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7])=[CH:4][N:3]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C(O)(C)C>[O:17]1[CH2:18][CH2:19][N:14]([C:2]2[CH:13]=[CH:12][C:5]([C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7])=[CH:4][N:3]=2)[CH2:15][CH2:16]1

参加物

4

反応物 2

HCID 8083MorpholineHCID 23512700Isopropyl 6-chloronicotinate

生成物 1

HCID 23512677Propan-2-yl 6-(morpholin-4-yl)pyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A solution of isopropyl 6-chloronicotinate (6.0 g, 0.03 mol) and morpholine (13 mL, 0.15 mol) in isopropyl alcohol (60 mL) was heated at reflux for 72 hours. The solution was allowed to cool to ambient temperature overnight. The resulting precipitate was isolated by filtration, washed with isopropyl alcohol and dried to provide isopropyl 6-morpholinonicotinate. The filtrate was diluted with water. The resulting precipitate was isolated by filtration, washed with water and dried to provide isopropyl 6-morpholinonicotinate. The combined yield was 8.3 g. The isopropyl 6-morpholinonicotinate was combined with 1 N sodium hydroxide (40 mL) and the resulting suspension was stirred at 50-60° C. until all of the solid had dissolved. The solution was stirred at ambient temperature overnight during which time a precipitate formed. This material was isolated by filtration and identified as starting material. The filtrate was neutralized with concentrated hydrochloric acid. The resulting precipitate was isolated by filtration, washed with water and dried to provide 3.3 g of crude product. This material was recrystallized from methanol/dichloromethane to provide 6-morpholinonicotinic acid as a solid, m.p. 259-261° C. Analysis: Calculated for C10H12N2O3: % C, 57.19; % H, 5.81; % N, 13.48; Found: % C, 57.50; % H, 5.71; % N, 13.53.

後処理

  1. temperatureat reflux for 72 hours
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with isopropyl alcohol
  4. customdried

出典と根拠

ORDレコード
ord-25aaef69605849b4aabe3a24730b1994
出典データセット
uspto-grants-2008_07
特許番号
US07393859B2

反応ノート

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