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

HRID 492689노트

반응식

HRID 492689 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 23925Iron촉매HCID 702Ethanol용매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dba73ec35ebe4f668dafec787244909d
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531532B2

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