5-Amino-1-naphthol → 5-methoxynaphthalen-1-amine

HRID 2075545Notes

Reaction equation

HRID 2075545 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12].[CH:13](N(C(C)C)CC)(C)C.[Si](C=[N+]=[N-])(C)(C)C>C(#N)C.CO.CCOCC>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[O:12][CH3:13]

Participants

7

Reactant 3

HCID 657465-Amino-1-naphtholHCID 81531DiisopropylethylamineHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 2355485-methoxynaphthalen-1-amineYield 63%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 10 g of 5-amino-1-hydroxynaphthalene in 250 ml of acetonitrile and 25 ml of methanol was added 15 ml of diisopropylethylamine followed by 44 ml of 2M TMSCHN2 in ether. The mixture was stirred at room temperature for 3.5 h after which it was concentrated to a dark oil. The material was purified by flash chromatography on silica gel, eluting with ethyl acetate/dichloromethane/heptane to provide 6.9 g (63%) of 5-amino-1-methoxynaphthalene.

Workup

  1. concentrationwas concentrated to a dark oil
  2. customThe material was purified by flash chromatography on silica gel
  3. washeluting with ethyl acetate/dichloromethane/heptane

Sources & evidence

ORD record
ord-06bcd6c8742a488ebc16f065a5fbaeef
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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