Stannous chloride dihydrate → 7-bromo-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one

HRID 1781018ノート

反応式

HRID 1781018 の反応式
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][CH2:10][C:11](O)=[O:12])=[C:4]([N+:14]([O-])=O)[CH:3]=1.BrC1C=C([N+]([O-])=O)C(F)=CC=1NCC(O)=O.O.O.[Sn](Cl)Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([NH:9][CH2:10][C:11](=[O:12])[NH:14]2)=[CH:6][C:7]=1[F:8]

参加物

5

反応物 3

HCID 61436Stannous chloride dihydrateHCID 100857532-[(4-Bromo-5-fluoro-2-nitrophenyl)amino]acetic AcidHCID 10469611N-(2-Bromo-5-fluoro-4-nitrophenyl)glycine

生成物 1

HCID 100374907-bromo-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of a mixture of N-(4'-bromo-5'-fluoro-2'-nitrophenyl)glycine and N-(2'-bromo-5'-fluoro-4'-nitrophenyl)glycine (0.150 g, 0.512 mmol, as prepared above) and tin (II) chloride dihydrate (0.346 g, 1.53 mmol, Aldrich, used as received) in ethanol (3.0 mL) was refluxed for 30 min. It was then cooled to room temperature and the solvent was removed under vacuum. The residue was diluted with water (10 mL) and basified with saturated NaHCO3 (3.0 mL) to pH ~8. The resulting white suspension was extracted with ethyl acetate (30 mL). The ethyl acetate was dried over anhydrous Na2SO4 and removed under vacuum to yield 0.050 g of crude product, which was purified by precipitation from ethanol:water (1:1) to give 30 mg (24%) of the pure (1H NMR) title compound as a light yellow powder; m.p. 172° C. (decomposed); 1H NMR (DMSO-d6): δ3.73 (s, 2H), 6.37 (s, 1H), 6.551 (d, 1H, J=10.2 Hz), 6.825 (d, 1H, J=6.6 Hz), 10.303 (s, 1H).

後処理

  1. temperaturewas refluxed for 30 min
  2. customthe solvent was removed under vacuum
  3. additionThe residue was diluted with water (10 mL)
  4. extractionThe resulting white suspension was extracted with ethyl acetate (30 mL)
  5. dry with materialThe ethyl acetate was dried over anhydrous Na2SO4
  6. customremoved under vacuum
  7. customto yield 0.050 g of crude product, which
  8. customwas purified by precipitation from ethanol:water (1:1)

出典と根拠

ORDレコード
ord-3b2d4eb0ed2e4dee9788780360db7fee
出典データセット
uspto-grants-1997_05
特許番号
US05631373

反応ノート

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