Water → N-[7-(Cyclopropylmethoxy)naphth-1-yl]acetamide

HRID 260668Notes

Reaction equation

HRID 260668 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[NH:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:19][CH:20]1[CH2:22][CH2:21]1.O>CS(C)=O>[CH:20]1([CH2:19][O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[NH:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=2)[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 80013(Chloromethyl)cyclopropaneHCID 809461-Acetamido-7-naphthol

Product 1

HCID 22400263N-[7-(Cyclopropylmethoxy)naphth-1-yl]acetamideYield 59.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

17.1 g (0.085 mol) of N-(7-hydroxynaphth-1-yl)acetamide in solution in 50 ml of dimethyl sulphoxide are added under a nitrogen atmosphere to a suspension of 3.4 g (0.085 mol) of sodium hydride in oil, washed beforehand with dry pentane), in 100 ml of dimethyl sulphoxide, while the mixture is cooled with an ice-water bath. Stirring is continued at room temperature for 2 h. 9.05 g (0.1 mol) of (chloromethyl)cyclopropane are added, and the mixture is stirred at room temperature for 4 h and left to stand overnight. The mixture is poured into 1 l of water, stirred for 1 h and left to stand overnight under cold conditions. The solid is separated by filtration, washed with water and dried. 13 g of a product melting point: 154°-155° C., are obtained which is used as it is in the following step.

Workup

  1. washwashed
  2. temperaturewhile the mixture is cooled with an ice-water bath
  3. stirringthe mixture is stirred at room temperature for 4 h
  4. waitleft
  5. waitto stand overnight
  6. stirringstirred for 1 h
  7. waitleft
  8. waitto stand overnight under cold conditions
  9. customThe solid is separated by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-f7008c6b03ac4d55ada0fd490ad51b40
Source dataset
uspto-grants-1996_06
Patent number
US05530002

Reaction notes

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