Methane → Methyl 5-amino-2-hydroxybenzoate

HRID 346235

反応式

HRID 346235 の反応式
[NH2:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.CO.B(F)(F)F.[CH3:18]COCC.C>C(Cl)Cl.O>[CH3:18][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=1[OH:11]

参加物

7

反応物 4

HCID 297MethaneHCID 887MethanolHCID 40755-Aminosalicylic AcidHCID 8000Boron trifluoride etherate

生成物 1

HCID 135127Methyl 5-amino-2-hydroxybenzoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 76.6 g (0.5 mole) of 5-aminosalicyclic acid in 252.0 g (8 mole) of methanol was added 150.0 g (1.06 mole) of borontrifluoride etherate (Aldrich) and the mixture was heated at reflux overnight. The reaction mixture was treated with 150 mL of water and filtered. The filtrate pH was adjusted to 8.4 with sodium bicarbonate, and the resulting solid was collected by filtration and air dried to give 43.0 g (51%) of crude title compound as a solid. A sample was dissolved in methylene chloride, treated with charcoal and filtered. The filtrate was concentrated under reduced pressure to give a solid. The solid was recrystallized from methylene chloride-petroleum ether (30°-60° C.) to give title compound as golden-brown needles, mp 95°-98° C.

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. filtrationthe resulting solid was collected by filtration and air
  5. customdried
  6. customto give 43.0 g (51%) of crude title compound as a solid
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a solid
  10. customThe solid was recrystallized from methylene chloride-petroleum ether (30°-60° C.)

出典と根拠

ORDレコード
ord-3185396ff96d4a239c19fa97a0dbbc88
出典データセット
uspto-grants-1991_10
特許番号
US05061720

関連ノート

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