Sodium Hydroxide → 3-(2,6-Dichloro-3-nitro-phenyl)-[1,6]naphthyridin-2-ylamine

HRID 270692노트

반응식

HRID 270692 반응식
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]#[N:14].[NH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[CH:22]=O.[OH-].[Na+]>CCO.CCOC(C)=O>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[C:13]([NH2:14])=[N:15][C:16]2[C:17]([CH:22]=1)=[CH:18][N:19]=[CH:20][CH:21]=2

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 27610334-AminonicotinaldehydeHCID 598338582-(2,6-Dichloro-3-nitrophenyl)acetonitrile

생성물 1

HCID 598339093-(2,6-Dichloro-3-nitro-phenyl)-[1,6]naphthyridin-2-ylamine수율 23.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2,6-dichloro-3-nitrophenyl-acetonitrile (1.02 g, 4.42 mmol), 4-amino-pyridine-3-carbaldehyde (0.4 g, 3.28 mmol) and NaOH (52 mg, 1.31 mmol) in EtOH (2.0 mL) is heated to 105° C. for 24 hours. The reaction mixture is diluted with EtOAc (50 ml) and washed with saturated K2CO3 and brine. The organic layer is dried, filtered and concentrated to give crude product. Flash silica gel column purification eluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (100/6) affords the titled intermediate as a solid (257 mg, 23.4%).

후처리

  1. washwashed with saturated K2CO3 and brine
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product
  6. customFlash silica gel column purification
  7. washeluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (100/6)

출처 및 근거

ORD 기록
ord-fe0cbafb60b9493d89f49b0b150ee853
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449582B2

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