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

HRID 492689ノート

反応式

HRID 492689 の反応式
[CH3:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[CH:6]=1.[Cl-].[NH4+].O>C(O)C.C(OCC)(=O)C.C(OCC)C.[Fe]>[NH2:24][C:22]1[CH:21]=[CH:20][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[O:13])[CH:6]=2)=[C:2]([CH3:1])[CH:23]=1

参加物

8

反応物 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 57677327N-[4-(2-Methyl-4-nitrophenoxy)-2-pyridinyl]-4-morpholinecarboxamide

生成物 1

HCID 57677565Morpholine-4-carboxylic acid [4-(4-amino-2-methylphenoxy)pyridin-2-yl]amide収率 26.1%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

To a solution of morpholine-4-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 20 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 then partitioned between ethyl acetate:tetrahydrofuran=1:1 (200 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, which was then suspended in ethyl acetate (5 ml), and diluted with diethyl ether (30 ml). The solid was filtered, and dried under aeration to provide the titled compound (184 mg, 26.1%) as colorless powder. The mother liquor was concentrated to give a residue, which was suspended in diethyl ether (30 ml). The solid was filtered, and dried under aeration to further provide the titled compound (207 mg, 29.3%) as pale yellow 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 then partitioned between ethyl acetate
  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, which
  12. filtrationThe solid was filtered
  13. customdried under aeration

出典と根拠

ORDレコード
ord-dba73ec35ebe4f668dafec787244909d
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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