Pyridine → 6-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 1846292

反応式

HRID 1846292 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N1C=CC=CC=1.Cl[C:20](Cl)([O:22]C(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C.ClCCl>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:20](=[O:22])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 2779305-Methoxyanthranilic acid

生成物 1

HCID 2944796-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
52.5 °C

実験手順

To a solution of 2-amino-5-methoxy-benzoic acid (1.50 g, 8.97 mmol) in anhydrous acetonitrile (15 mL) at 50-55° C. were simultaneously added pyridine (1.42 g, 17.9 mmol) and a solution of triphosgene (0.870 g, 2.96 mmol) in anhydrous dichloromethane (20 mL) over 20 min span, and the reaction was stirred at 50-55° C. for 2 hours. The solvent was removed and the residue was mixed with water (100 mL), the solid was filtered and rinsed with cold water (30 mL) and dried. The crude was further washed with ether (20 mL) to give 6-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione. Yield: 1.55 g (89%).

後処理

  1. customat 50-55° C.
  2. customThe solvent was removed
  3. additionthe residue was mixed with water (100 mL)
  4. filtrationthe solid was filtered
  5. washrinsed with cold water (30 mL)
  6. customdried
  7. washThe crude was further washed with ether (20 mL)

出典と根拠

ORDレコード
ord-920fd3a8e1bc43f494e89e5f1d9170f1
出典データセット
uspto-grants-2015_02
特許番号
US08952021B2

関連ノート

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