Methyl Isocyanate → 1-Methylcarbamoyloxy-2,4-dimethoxynaphthalene

HRID 845548

Reaction equation

HRID 845548 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[O:14][CH3:15].[CH3:16][N:17]=[C:18]=[O:19]>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:16][NH:17][C:18]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[O:14][CH3:15])=[O:19]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 125635471-Hydroxy-2,4-dimethoxynaphthalene

Product 1

HCID 141830391-Methylcarbamoyloxy-2,4-dimethoxynaphthalene

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.00 g of 1-hydroxy-2,4-dimethoxynaphthalene, prepared as shown in Preparations 7 and 8, in 50 ml of tetrahydrofuran was added 0.335 g of methyl isocyanate followed by 0.12 g of 4-dimethylaminopyridine. The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate, washed with dilute hydrochloric acid and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue chromatographed on silica gel, eluting with methylene chloride, giving 1-methylcarbamoyloxy-2,4-dimethoxynaphthalene, m.p. 131°-133° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with dilute hydrochloric acid
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue chromatographed on silica gel
  7. washeluting with methylene chloride

Sources & evidence

ORD record
ord-2154a6d05d3442fc9cf7020a8932402c
Source dataset
uspto-grants-1988_07
Patent number
US04758587

Linked notes

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