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

HRID 1846292노트

반응식

HRID 1846292 반응식
[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

참가 물질

6

반응물 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 2779305-Methoxyanthranilic acid

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

반응 조건

온도
52.5 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-920fd3a8e1bc43f494e89e5f1d9170f1
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952021B2

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