Water → Pyrrolidine-1-carboxylic acid [4-(4-amino-2-methylphenoxy)pyridin-2-yl]amide

HRID 492691ノート

反応式

HRID 492691 の反応式
[CH3:1][C:2]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])[CH:6]=1.[Cl-].[NH4+].O.C(OCC)(=O)C>C(O)C.[Fe]>[NH2:23][C:21]1[CH:20]=[CH:19][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:13])[CH:6]=2)=[C:2]([CH3:1])[CH:22]=1

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 57677612N-[4-(2-Methyl-4-nitrophenoxy)-2-pyridinyl]-1-pyrrolidinecarboxamide

生成物 1

HCID 57677322Pyrrolidine-1-carboxylic acid [4-(4-amino-2-methylphenoxy)pyridin-2-yl]amide収率 66.2%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of pyrrolidine-1-carboxylic acid [4-(2-methyl-4-nitrophenoxy)pyridin-2-yl]amide (775 mg) in ethanol (50 ml) were added electrolytic iron powder (505 mg), ammonium chloride (967 mg) and water (10 ml), followed by stirring to heat at 90° C. for 30 min. The reaction mixture was cooled down to room temperature, and filtered to remove an insoluble portion, which was then washed with water and N,N-dimethylformamide in this order. The filtrate was concentrated under a reduced pressure to give a residue, which was partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, to which ethyl acetate (10 ml) was added, followed by allowing to stand at room temperature. After a solid precipitated, diethyl ether (30 ml) was added thereto, followed by stirring at room temperature for 2 hrs. The solid was filtered off, and dried under aeration to provide the titled compound (467 mg, 66.2%) as powder.

後処理

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationfiltered
  3. customto remove an insoluble portion, which
  4. washwas then washed with water and N,N-dimethylformamide in this order
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customto give a residue, which
  7. customwas partitioned between ethyl acetate (100 ml) and water (100 ml)
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated
  11. customto give a residue
  12. customto stand at room temperature
  13. customAfter a solid precipitated
  14. additiondiethyl ether (30 ml) was added
  15. stirringby stirring at room temperature for 2 hrs
  16. filtrationThe solid was filtered off
  17. customdried under aeration

出典と根拠

ORDレコード
ord-2a5c242af70e4346868883b5aa10fa1d
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

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