4-(2-Benzyloxy-naphthalen-1-yl)-oxazol-2-ylamine → 1-(2-Amino-oxazol-4-yl)-naphthalen-2-ol

HRID 33568Notes

Reaction equation

HRID 33568 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[C:19]1[N:20]=[C:21]([NH2:24])[O:22][CH:23]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH2:24][C:21]1[O:22][CH:23]=[C:19]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[CH:18][C:9]=2[OH:8])[N:20]=1

Participants

5

Reactant 2

HCID 597968544-(2-Benzyloxy-naphthalen-1-yl)-oxazol-2-ylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 597968451-(2-Amino-oxazol-4-yl)-naphthalen-2-olYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(2-Benzyloxy-naphthalen-1-yl)-oxazol-2-ylamine (12, 1.0 g) was dissolved in ethanol and then palladium, 10% on carbon (390 mg) was added. The mixture was stirred under 1 atmosphere of hydrogen for 48 hours. The mixture was filtered through a pad of hyflo and washed with industrial methylated spirits. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography to afford 1-(2-amino-oxazol-4-yl)-naphthalen-2-ol (22) (290 mg, 41%) as a glassy orange foam. 1H NMR (DMSO-D6): 6.6 (2H, br s), 6.85 (1H, s), 7.2 (1H, d, J=9.0 Hz), 7.25 (1H, m), 7.4 (1H, m), 7.75 (2H, m), 7.9 (1H, m), 9.9 (1H, br s). Mass Spectrum (m/z): 227 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a pad of hyflo
  2. washwashed with industrial methylated spirits
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a66f43212c0646d48d25e035aa427cf0
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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