Hydrochloric Acid → 1,2,3,4-Tetrahydro-4-methoxy-1-naphthylurea

HRID 372281Notes

Reaction equation

HRID 372281 reaction equation
[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([NH:12][C:13]([NH2:15])=[O:14])[CH2:4][CH2:3]1.[H-].[Na+].[CH3:18]I.Cl>CN(C)C=O>[CH3:18][O:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([NH:12][C:13]([NH2:15])=[O:14])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 42945181,2,3,4-Tetrahydro-4-hydroxy-1-naphthylurea

Product 1

HCID 203273121,2,3,4-Tetrahydro-4-methoxy-1-naphthylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 2.0 g sample of 1,2,3,4-tetrahydro-4-hydroxy-1-naphthylurea (cis/trans) is stirred in 10 ml of dry dimethylformamide and one equivalent of sodium hydride in mineral oil added at 0° C under a nitrogen atmosphere. After the addition is completed, 1.2 equivalents of methyl iodide is added and the reaction mixture stirred overnight. The mixture is carefully poured on ice, neutralized with hydrochloric acid and the title compound collected by filtration. Evaporation of the filtrate to dryness and washing the residue with water affords additional title compound.

Workup

  1. additionAfter the addition
  2. additionThe mixture is carefully poured on ice
  3. filtrationthe title compound collected by filtration
  4. customEvaporation of the filtrate to dryness
  5. washwashing the residue with water

Sources & evidence

ORD record
ord-7e3a9aa6ebad4457a285fc2d2149992a
Source dataset
uspto-grants-1978_05
Patent number
US04089976

Reaction notes

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