Water → t-Butyl 2-(6-cyano-2-naphthyloxy)-5-nitrobenzoate

HRID 895712Notes

Reaction equation

HRID 895712 reaction equation
F[C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:18]([C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([OH:30])[CH:24]=[CH:23]2)#[N:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:18]([C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([O:30][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH:24]=[CH:23]2)#[N:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 45894766-Hydroxy-2-naphthonitrileHCID 22380964Tert-butyl 2-fluoro-5-nitrobenzoate

Product 1

HCID 22380917t-Butyl 2-(6-cyano-2-naphthyloxy)-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (t-butyl 2-fluoro-5-nitrobenzoate) (1.74 g) obtained in a previous production example, 6-cyano-2-naphthol (1.86 g) and potassium carbonate (8.2 g) were heated to 50° C. in N,N-dimethylformamide and reacted for 2 hours. After cooling to room temperature, water was added and extraction was performed with ethyl acetate. The ethyl acetate layer was washed with saturated saline and dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography (300 g, hexane:ethyl acetate=5:1) to obtain 3.23 g of t-butyl 2-(6-cyano-2-naphthyloxy)-5-nitrobenzoate.

Workup

  1. customreacted for 2 hours
  2. extractionextraction
  3. washThe ethyl acetate layer was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel chromatography (300 g, hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-963d3e736c7340afb56855abd981d7af
Source dataset
uspto-grants-2005_07
Patent number
US06916837B2

Reaction notes

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