Triethylamine → HCID 20427002、化合物

HRID 615690ノート

反応式

HRID 615690 の反応式
N[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:6].C(N(CC)CC)C.[C:24](Cl)(=[O:27])[CH2:25][CH3:26].[OH-].[Na+]>O.CC(C)=O>[C:24]([C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:6])(=[O:27])[CH2:25][CH3:26]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 62324Propionyl chlorideHCID 5775803-Amino-N-2-pyridinylbenzamide

生成物 1

HCID 20427002HCID 20427002、化合物収率 91.7%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

To a mixture of 2-aminopyridine (28.2 g), triethylamine (45 ml) and acetone (600 ml), 3-nitrobenzoyl chloride (55.8 g) was gradually added with stirring under ice cooling. The mixture was stirred for 30 minutes under the same condition, then for one hour at room temperature. Thereafter, the reaction solution was poured into 3 liters of water, and the resulting crystal was collected by filtration, washed with water, and recrystallized from methanol to provide 58.5 g of 3-nitro-N-2-pyridylbenzamide as a colorless acicular crystal (yield: 80%, m.p. 156°-157° C.). Hydrogen was bubbled into a mixture of the 3-nitro-N-2-pyridylbenzamide (15.9 g), 10% palladium-carbon (1.5 g) and ethanol (300 ml). After a stoichiometric amount of hydrogen was absorbed, the catalyst was removed, the reaction mixture was concentrated under vacuum, and the residue was recrystallized from ethanol to provide 7.2 g of a colorless acicular crystal of 3-amino-N-2-pyridylbenzamide (yield: 52%, m.p. 113°-115° C.). To a mixture of the 3-amino-N-2-pyridylbenzamide (6.4 g), triethylamine (4.5 ml) and acetone (60 ml), propionic acid chloride (2.8 g) was gradually added with stirring at room temperature. After one hour of stirring, the reaction mixture was poured into 200 ml of water which was then made weakly alkaline by gradually adding a 10% solution of sodium hydroxide. The resulting crystal was collected by filtration, washed with water and recrystallized from methanol to provide 7.0 g of 3-propionyl-N-2-pyridylbenzamide as a colorless acicular crystal (compound 1) (yield: 87%, m.p. 128°-129° C.).

後処理

  1. additionwas gradually added
  2. stirringAfter one hour of stirring
  3. filtrationThe resulting crystal was collected by filtration
  4. washwashed with water
  5. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-94e25520e60a492b8e8947775f99d768
出典データセット
uspto-grants-1985_02
特許番号
US04500714

反応ノート

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