Ammonium formate → 1-[4-(2-Azepan-1-yl-ethoxy)-phenoxy]-6-methoxy-naphthalen-2-ol

HRID 1513870Notes

Reaction equation

HRID 1513870 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]=1[O:21][C:22]1[CH:37]=[CH:36][C:25]([O:26][CH2:27][CH2:28][N:29]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:24][CH:23]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(OCC)(=O)C.CO.[Pd]>[N:29]1([CH2:28][CH2:27][O:26][C:25]2[CH:24]=[CH:23][C:22]([O:21][C:10]3[C:11]4[C:16](=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=4)[CH:17]=[CH:18][C:9]=3[OH:8])=[CH:37][CH:36]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 2

HCID 2723923Ammonium formate2×HCID 670044981-{2-[4-(2-Benzyloxy-6-methoxy-naphthalen-1-yloxy)-phenoxy]ethyl}-azepane

Product 1

HCID 670047881-[4-(2-Azepan-1-yl-ethoxy)-phenoxy]-6-methoxy-naphthalen-2-olYield 97.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 1-{2-[4-(2-benzyloxy-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}-azepane (19 g, 38 mmol) in ethyl acetate (500 mL) and methanol (600 ml Heat the mixture to obtain a clear solution. Cool to room temperature. Add ammonium formate (30 g, 476 mmol) and palladium on carbon (2 g, 1.9 mmol). Heat to reflux for 30 minutes. Add ammonium formate (7 g, 111 mmol) and palladium on carbon (0.7 g, 0.7 mmol). Heat to reflux for 30 minutes. Filter the suspension through a pad of celite and elute with ethyl acetate (500 mL). Evaporate solvent under reduced pressure and add water (100 mL). Dilute the mixture with ethyl acetate (500 mL) and separate layers. Wash the organic layer with saturated sodium bicarbonate solution (2×200 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to give 15.1 g (97%) of 1-[4-(2-azepan-1-yl-ethoxy)-phenoxy]-6-methoxy-naphthalen-2-ol.

Workup

  1. temperatureHeat the mixture
  2. customto obtain a clear solution
  3. temperatureHeat
  4. temperatureto reflux for 30 minutes
  5. temperatureHeat
  6. temperatureto reflux for 30 minutes
  7. filtrationFilter the suspension through a pad of celite
  8. washelute with ethyl acetate (500 mL)
  9. additionEvaporate solvent under reduced pressure and add water (100 mL)
  10. additionDilute the mixture with ethyl acetate (500 mL)
  11. customseparate layers
  12. washWash the organic layer with saturated sodium bicarbonate solution (2×200 mL)
  13. dry with materialdry with magnesium sulfate
  14. filtrationfilter
  15. customevaporate solvent under reduced pressure

Sources & evidence

ORD record
ord-6180d7a1ad194be3b0d7f44e58ed1234
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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