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

HRID 1988890ノート

反応式

HRID 1988890 の反応式
[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

参加物

8

反応物 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 546962297-Bromo-4-hydroxycoumarin2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒2 回HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fcc71233e32c490bacd2ec98429cdf32
出典データセット
uspto-grants-2010_01
特許番号
US07642276B2

反応ノート

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