Hydrochloric Acid → HCID 67119420、化合物

HRID 384832ノート

反応式

HRID 384832 の反応式
O.Cl.[CH3:3][C:4]1[C:15]([O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)=[CH:14][C:7]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])=[C:6]([N+:28]([O-])=O)[CH:5]=1.C(=O)(O)[O-].[Na+]>C(O)C.[Fe]>[NH2:28][C:6]1[CH:5]=[C:4]([CH3:3])[C:15]([O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:26])[F:27])=[CH:19][CH:18]=2)=[CH:14][C:7]=1[C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 67119435HCID 67119435、化合物

生成物 1

HCID 67119420HCID 67119420、化合物収率 82.2%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒2 回

反応条件

温度
70 °C

実験手順

An iron powder (372.9 g), 1290 ml of ethanol, 531 ml of water, and 2.8 g of a 35% hydrochloric acid were charged into a 2000-ml glass flask equipped with a stirring device, a thermometer, and a reflux condenser, and the mixture was heated to reflux. Isopropyl 4-methyl-2-nitro-5-(4-(trifluoromethoxy)phenoxy)benzoate (373 g) dissolved in 398 ml of ethanol was added dropwise thereto over a period of two hr. After reflux for 8 hr, 10 ml of a saturated aqueous sodium bicarbonate solution was added, and the mixture was filtered. The filtrate was concentrated, and 300 ml of ethyl acetate was added to the residue. The mixture was washed with brine, followed by separation. The ethyl acetate layer was concentrated under the reduced pressure. Isopropanol (320 ml) was added to the residue, and the mixture was heated at 70° C. for dissolution. Water (160 ml) was added to the solution to cool the solution. The precipitated solid was collected by filtration and was dried to give isopropyl 2-amino-4-methyl-5-(4-(trifluoromethoxy)phenoxy)benzoate (283.7 g, yield: 82.2%).

後処理

  1. customequipped with a stirring device
  2. temperaturea thermometer, and a reflux condenser, and the mixture was heated to reflux
  3. additionwas added dropwise
  4. temperatureAfter reflux for 8 hr
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated
  7. addition300 ml of ethyl acetate was added to the residue
  8. washThe mixture was washed with brine
  9. customfollowed by separation
  10. concentrationThe ethyl acetate layer was concentrated under the reduced pressure
  11. additionIsopropanol (320 ml) was added to the residue
  12. additionWater (160 ml) was added to the solution
  13. temperatureto cool the solution
  14. filtrationThe precipitated solid was collected by filtration
  15. customwas dried

出典と根拠

ORDレコード
ord-689ead90ee1d4fedaffb808f1716e379
出典データセット
uspto-grants-2013_02
特許番号
US08367833B2

反応ノート

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