Naphthalen-1-ethanol → HCID 22504197, compound

HRID 1814308Notes

Reaction equation

HRID 1814308 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([NH2:7])=[O:6].[C:14]1([CH2:24][CH2:25][OH:26])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[K+]>O1CCCC1.C(OCC)(=O)C>[C:14]1([CH2:24][CH2:25][O:26][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=2[N+:11]([O-:13])=[O:12])[C:5]([NH2:7])=[O:6])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 13047Naphthalen-1-ethanolHCID 114239673-Fluoro-4-nitrobenzamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 22504197HCID 22504197, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-fluoro-4-nitro-benzamide (1.0 g, 5.43 mmol) in tetrahydrofuran (55 mL) at room temperature was added 1-napthaleneethanol (1.02 g, 5.97 mmol) followed by potassium tert-butoxide (0.67 g, 5.97 mmol). The reaction was allowed to stir overnight at room temperature. The reaction was then diluted with ethyl acetate and washed with 1N hydrochloric acid (50 mL), saturated sodium bicarbonate (50 mL), and saturated sodium chloride (50 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield a pale yellow solid. The powder was collected and washed with ether, followed by drying under reduced pressure to yield 3-(2-naphthalen-1-yl-ethoxy)-4-nitro-benzamide 1.09 g (60%). 1HNMR(300 MHz, DMSO) 8.13 (d, 2H), 7.91 (t, 2H), 7.88 (dd, 1H), 7.72(s, 1H), 7.64 (s, 1H), 7.41 (m, 5H), 4.50 (t, 2H), 3.54 (t, 2H). MS(APCI) m/z 335.1 (M−H). Anal. Calcd. for C19H16N2O4: C, 67.85; H, 4.79; N, 8.33. Found: C, 67.35; H, 4.53; N, 8.06.

Workup

  1. washwashed with 1N hydrochloric acid (50 mL), saturated sodium bicarbonate (50 mL), and saturated sodium chloride (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield a pale yellow solid
  6. customThe powder was collected
  7. washwashed with ether
  8. customby drying under reduced pressure

Sources & evidence

ORD record
ord-fd60dd7b3355403dbde60cf5fdc506d4
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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