Methyl iodide → 8-Amino-2-naphthalenol

HRID 719181

Reaction equation

HRID 719181 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9](S(O)(=O)=O)[CH:8]=[CH:7]2.[NH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[CH:25]=[C:24]([OH:27])[CH:23]=[CH:22]2.[H-].[Na+].CI>CN(C)C=O.O>[NH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[CH:25]=[C:24]([OH:27])[CH:23]=[CH:22]2.[CH3:24][O:27][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][CH:3]=[C:2]2[NH2:1])=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 83588-Amino-2-naphthalenolHCID 8386Cleve's acidHCID 24758Sodium hydride

Product 2

HCID 83588-Amino-2-naphthalenolHCID 2358177-Methoxynaphthalen-1-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

8-Amino-naphthalen-2-ol was prepared from 8-amino-2-naphthalenesulphonic acid (commercially available) according to the literature (J. Org. Chem. 1949, p351). To a solution of 8-amino-naphthalen-2-ol (8.00 g) in dry N,N-dimethylformamide (80 mL) was added sodium hydride (60% dispersion in mineral oil, 3.2 g) carefully. After stirring for 4 hours the reaction mixture was cooled in an ice bath and methyl iodide (3.13 mL) was added dropwise. The reaction mixture was then stirred at room temperature for 3 days. Water (10 mL) was then added and the volatiles were removed in vacuo. The residue was dissolved in chloroform, washed with water, dried (MgSO4) and the solvent removed in vacuo to yield a dark oil. This was purified using flash chromatography (chloroform) to yield 7-methoxy-naphthalen-1-ylamine as a dark brown liquid (2.92 g).

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringThe reaction mixture was then stirred at room temperature for 3 days
  3. customthe volatiles were removed in vacuo
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customto yield a dark oil
  9. customThis was purified

Sources & evidence

ORD record
ord-d39c13159e5342e598803700f91173f1
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Linked notes

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