Water → 1-Naphthylamine

HRID 541169Notes

Reaction equation

HRID 541169 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)([O-])=O.O>C(OCC)(=O)C>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 962WaterHCID 68491-Nitronaphthalene

Product 1

HCID 86401-NaphthylamineYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

86.6 mg (0.50 mmol) of 1-nitronaphthalene (17), 270 μL (15 mmol) of distilled water and stainless steel balls (50 pieces) were placed in the vessel of the planetary ball mill, which was then closed, and agitated by operating the planetary ball mill for 12 hours at 800 rpm (reversed every 30 minutes). After the lapse of 12 hours, 10 mL of ethyl acetate was added to the vessel of the planetary ball mill to provide a solution containing the reaction mixture, which was then filtered with celite. The operation was repeated 5 times to provide a filtrate, which was then concentrated, thereby providing 44.3 mg (0.31 mmol) of 1-aminonaphthalene (18). The yield was 62%. The conversion yield was 100%, but the isolated yield was lowered since the product was partially distilled off under reduced pressure. The reaction is expressed by the following scheme.

Workup

  1. customwas then closed
  2. customfor 12 hours
  3. customto provide a solution
  4. additioncontaining the reaction mixture, which
  5. filtrationwas then filtered with celite
  6. customto provide a filtrate, which
  7. concentrationwas then concentrated

Sources & evidence

ORD record
ord-6ce55f82bdaa4c479184c2720db64d59
Source dataset
uspto-grants-2014_10
Patent number
US08871980B2

Reaction notes

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