Hydroxyamine hydrochloride → 2-(6-Bromo-1,2-benzoxazol-3-yl)acetic acid

HRID 1988890노트

반응식

HRID 1988890 반응식
[Na].Cl.[NH2:3][OH:4].[Br:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](O)=[CH:11][C:12](=[O:16])[O:13]2)=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>C(O)C.ClCCl.O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]([CH2:11][C:12]([OH:16])=[O:13])=[N:3][O:4][C:14]=2[CH:15]=1

참가 물질

8

반응물 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 546962297-Bromo-4-hydroxycoumarin2회

생성물 1

HCID 591273762-(6-Bromo-1,2-benzoxazol-3-yl)acetic acid수율 76.8%

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Sodium metal (0.36 g) was dissolved in dry ethanol (30 ml) then treated with hydroxylamine hydrochloride (1.12 g). A solution of 7-bromo-4-hydroxy-2H-chromen-2-one (Intermediate 31) (1.3 g) in dry ethanol (30 ml) was added and the mixture was stirred at reflux under nitrogen for 3.5 h. On cooling the mixture was added to 2M aqueous sodium bicarbonate (100 ml). Water (100 ml) and dichloromethane (100 ml) were added, the phases were separated and the aqueous layer was washed with more dichloromethane (75 ml). The aqueous layer was acidified by the cautious addition of 2N hydrochloric acid to yield a precipitate which was collected by filtration and dried to give the title compound as a white solid (1.06 g).

후처리

  1. temperatureat reflux under nitrogen for 3.5 h
  2. temperatureOn cooling the mixture
  3. customthe phases were separated
  4. washthe aqueous layer was washed with more dichloromethane (75 ml)
  5. additionThe aqueous layer was acidified by the cautious addition of 2N hydrochloric acid
  6. customto yield a precipitate which
  7. filtrationwas collected by filtration
  8. customdried

출처 및 근거

ORD 기록
ord-fcc71233e32c490bacd2ec98429cdf32
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642276B2

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