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

HRID 270692Notes

Reaction equation

HRID 270692 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-fe0cbafb60b9493d89f49b0b150ee853
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Reaction notes

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