Methyl iodide → 5-methoxynaphthalen-1-amine

HRID 1470508Notes

Reaction equation

HRID 1470508 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[OH:14].I[CH3:16]>CN(C=O)C>[CH3:16][O:14][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[CH:12][CH:13]=[C:4]2[NH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 657465-Amino-1-naphthol

Product 1

HCID 2355485-methoxynaphthalen-1-amineYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of NaH (7.5 g, 188.0 mmol) in DMF (500 mL) was added a solution of 5-amino-1-naphthol (25.0 g, 157 mmol) dropwise at 0° C. After the addition, mixture was stirred for 30 min at 0° C. and for 1 h at RT. Then a solution of iodomethane (9.82 mL, 157 mmol) in DMF (25 mL) was added dropwise to the mixture at 0° C. and the reaction mixture was allowed to RT and stirred overnight. It was slowly quenched with ice and extracted with EtOAc. The combined organic layers were washed with water, brine, and dried. The solvent was removed under reduced pressure and the residue was purified by column chromatography to afford the title compound (23.0 g, 85%).

Workup

  1. additionAfter the addition, mixture
  2. customwas allowed to RT
  3. stirringstirred overnight
  4. customIt was slowly quenched with ice
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with water, brine
  7. customdried
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c92d12122f1e4cfdb62dfe09e77af18d
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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