Azide → 1-Naphthol

HRID 1938822Notes

Reaction equation

HRID 1938822 reaction equation
C([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+]([O-])=O)=[CH:6][CH:5]=1)=O.[N-]=[N+]=[N-].C(N([CH:22]([CH3:24])[CH3:23])CC)(C)C.[C:25](OCC)(=O)C.CO>CN(C=O)C>[CH:24]1[CH:22]=[CH:23][C:5]2[C:6](=[CH:7][CH:8]=[CH:9][C:4]=2[OH:3])[CH:25]=1

Participants

6

Reactant 4

HCID 33558AzideHCID 746284-Nitrophenyl formateHCID 81531DiisopropylethylamineHCID 21584119Ethylacetate methanol

Product 1

HCID 70051-Naphthol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.6 mgs of p-nitrophenyl formate was added to a stirred solution of 22.4 mgs of the amine (i) and 7 microliters of diisopropylethyl amine in 2 ml of DMF. The resulting mixture was stirred overnight at room temperature, partitioned between ethyl acetate and water. Aqueous workup and purification of the crude reaction product by column chromatography on silica gel using ethyl acetate/methanol (10:1) as the eluant gave the desired formamide (ii) (15.8 mg) as a white solid. FABMS MH+, 653.2.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customAqueous workup and purification of the crude
  3. customreaction product by column chromatography on silica gel

Sources & evidence

ORD record
ord-2d4657e8d1f64d33aaa0742f10c92a1a
Source dataset
uspto-grants-1997_12
Patent number
US05693815

Reaction notes

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