Chlorosuccinimide → HCID 11289654, compound

HRID 1830688Notes

Reaction equation

HRID 1830688 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.C1C(=O)N([Cl:28])C(=O)C1>C1COCC1>[Cl:28][C:10]1[C:11]2[C:6](=[CH:5][C:4]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[CH:3][C:2]=2[F:1])[CH:7]=[CH:8][C:9]=1[OH:12]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11311694HCID 11311694, compound

Product 1

HCID 11289654HCID 11289654, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-fluoro-6-(4-methoxyphenyl)-2-naphthol (0.17 g, 0.63 mmol) and NCS (0.10 g, 0.76 mmol) in THF (20 mL) were stirred under nitrogen at room temperature overnight according to Method C. The solution was concentrated onto Florosil and purified on a silica column (20% ethyl acetate-hexanes) to yield 0.16 g (84%) of the. title compound as a yellow solid. An analytical sample was further prepared by preparative reverse phase HPLC to yield a light yellow solid: mp 120–124° C.; 1H NMR (DMSO-d6): δ 3.82 (3H, s), 7.06 (2H, d, J=8.80 Hz), 7.34 (1H, d, J=8.91 Hz), 7.67 (1H, dd, J=1.69 Hz, J=15.48 Hz), 7.78 (2H, d, J=8.78 Hz), 8.01 (1H, d, J=1.54 Hz), 10.62 (1H, s); MS (ESI) m/z 301/303 (M−H)−.

Workup

  1. concentrationThe solution was concentrated onto Florosil
  2. custompurified on a silica column (20% ethyl acetate-hexanes)
  3. customto yield 0.16 g (84%) of the

Sources & evidence

ORD record
ord-2636acf7c04f4f74bfca0e387e78f1aa
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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