Acetone → 2-Chloroquinoline-4-carbonyl azide

HRID 47448

反応式

HRID 47448 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](Cl)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.ClC1C=C(C(O)=O)C2C(=CC=CC=2)N=1.[N-:29]=[N+:30]=[N-:31].[Na+].CC(C)=O>O1CCOCC1.O>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([N:29]=[N+:30]=[N-:31])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

参加物

7

反応物 4

HCID 180AcetoneHCID 33557Sodium AzideHCID 754382-Chloroquinoline-4-carbonyl chlorideHCID 2305822-Chloroquinoline-4-carboxylic acid

生成物 1

HCID 227451412-Chloroquinoline-4-carbonyl azide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

2-Chloro-4-chlorocarbonylquinoline (0.5 g), prepared by standard methods from 2-chloroquinoline-4-carboxylic acid, was added to sodium azide in aqueous dioxan (2.1 ml 1:3) at 0° C. Acetone was then added and the mixture stirred for 16 h. Water (10 ml) was added, the precipitated solid collected by filtration and air dried to give 2-chloroquinoline-4-carbonyl azide (0.455 g). The azide (0.232 g) in toluene (10 ml) was warmed from room temperature to 75° C. and then heating continued for 1 h. After cooling to room temperature 6-amino-2-methylbenzoxazole (0.148 g) in dichloromethane (15 ml) containing 4-N,N-dimethylaminopyridine (20 mg) was added and the mixture stirred for 16 h. The precipitated solid was separated by filtration to give a solid (0.25 g). Column chromatography (silica gel, dichloromethane/methanol/ammonia mixtures) gave the title compound (0.072 g). 1H NMR δ: 5 2.60 (3H, s), 7.25 (1H, d, J=8.5 Hz), 7.61 (1H, d, J=8.5 Hz), 7.73 (1H, t, J=7.0 Hz), 7.84 (1H, t, J=6.7 Hz), 7.91 (1H, d, J=8.0 Hz), 8.05 (1H, s), 8.20 (1H, d, J=8.25 Hz), 8.28 (1H, s), 9.49 (1H, s), 9.61 (1H, s). m/z (API+): 353, 355(MH+).

後処理

  1. filtrationthe precipitated solid collected by filtration and air
  2. customdried

出典と根拠

ORDレコード
ord-fed1940bbfb744c0a7d8ffbbe771e0bf
出典データセット
uspto-grants-2004_03
特許番号
US06699879B1

関連ノート

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