Sodium hydride → HCID 22337893, compound

HRID 585600Notes

Reaction equation

HRID 585600 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:20]([OH:24])=[CH:19][CH:18]=[CH:17][C:16]=2[CH:15]=1.[H-].[Na+]>CN(C)C=O>[NH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[O:24][CH2:2][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 703202-BromomethylnaphthaleneHCID 902956-Aminonaphthol

Product 1

HCID 22337893HCID 22337893, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromomethylnaphthalene (4.60 g) is added to a mixture of 2-Amino-5-naphthol (3.34 g) and sodium hydride (1.00 g) in dimethylformamide (100 mL) at −40 deg. C. Let stir overnight at room temperature. Concentrate in vacuo. Redilute with ethylacetate and absorb onto silica gel. Chromatograph (ethyl acetate/hexane) to give 2-amino-5-(Naphthalen-2-ylmethoxy)-naphthalene (1.86 g, 30%). Without further characterization this amine and triethylamine (0.90 mL) were dissolved in dichloromethane (75 mL). Cooled in an acetone and dry ice bath. Triflic anhydride (1.05 mL) was added and the mixture had warmed to room temperature overnight. Partition between water and ethyl acetate. Separate and dry with magnesium sulfate. Concentrate at rotovap, and triturate with ethyl acetate to provide the title compound (0.825 g, 30%) as a pale yellow solid, m.p. 140-142° C. 1H NMR (DMSO-d6, 400 MHz): δ 5.47 (s, 2H), 7.12 (d, 1H), 7.40-7.56 (m, 5H), 7.67 (d, 1H), 7.75 (s, 1H), 7.91-7.98 (m, 3H), 8.09 (s, 1H), 8.30 (d, 1H). MS [EI, m/z]: 430 [M−H]+. Anal. Calcd. for C22H16F3NO3S: C, 61.25; H, 3.74; N, 3.25. Found: C, 61.05; H, 3.81; N, 3.12.

Workup

  1. concentrationConcentrate in vacuo
  2. additionRedilute with ethylacetate
  3. customabsorb onto silica gel

Sources & evidence

ORD record
ord-e93f3b287a924ef3bb2b1bfa703c447a
Source dataset
uspto-grants-2005_08
Patent number
US06933322B2

Reaction notes

Loading…