Ammonium Chloride → 6-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1184337ノート

反応式

HRID 1184337 の反応式
[Cl-].[NH4+].[F:3][C:4]1([F:22])[O:9][C:8]2[CH:10]=[C:11]([F:17])[C:12]([N+:14]([O-])=O)=[CH:13][C:7]=2[N:6]([CH2:18][C:19]#[CH:20])[C:5]1=[O:21]>O.CO.O1CCCC1.[Fe]>[NH2:14][C:12]1[C:11]([F:17])=[CH:10][C:8]2[O:9][C:4]([F:3])([F:22])[C:5](=[O:21])[N:6]([CH2:18][C:19]#[CH:20])[C:7]=2[CH:13]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 871738852,2,7-trifluoro-6-nitro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

生成物 1

HCID 866695376-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one収率 81.5%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 962Water溶媒HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To ammonium chloride (3.96 g, 74.0 mmol) in water was added iron powder (325 mesh; 4.13 g, 74.0 mmol). To the resulting mixture was added 2,2,7-trifluoro-6-nitro-4-(prop-2-ynyl)-2Hbenzo[b][1,4]oxazin-3(4H)-one (7.06 g, 24.67 mmol) in methanol/tetrahydrofuran. The resulting mixture was stirred vigorously at 70° C. for 2 hours. The reaction was quenched in water/ethyl acetate under stirring. The resulting 2 phase system was filtered and the layers were separated. The water layer was subsequently extracted with ethyl acetate. The combined organic phases were washed with brine, dried with Na2SO4 and concentrated to yield 5.15 g of the title compound.

後処理

  1. customThe reaction was quenched in water/ethyl acetate
  2. stirringunder stirring
  3. filtrationThe resulting 2 phase system was filtered
  4. customthe layers were separated
  5. extractionThe water layer was subsequently extracted with ethyl acetate
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-41a40375dbf64d3b8ff7b0356caed302
出典データセット
uspto-grants-2014_03
特許番号
US08669208B2

反応ノート

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