1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Hydroxy-6-methoxy-2-naphthalenecarboxylic acid, methyl ester

HRID 35664Notes

Reaction equation

HRID 35664 reaction equation
Br[C:2]1([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]1=[O:14].N12CCCN=C1CCCCC2>O1CCCC1>[OH:14][C:3]1[C:4]2[C:9](=[CH:8][C:7]([O:12][CH3:13])=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 14256768HCID 14256768, compound

Product 1

HCID 142567481-Hydroxy-6-methoxy-2-naphthalenecarboxylic acid, methyl esterYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10.2 g (0.033 mole) of 1,2,3,4-tetrahydro-2-bromo-6-methoxy-1-oxo-2-naphthalenecarboxylic acid, methyl ester in 100 ml of tetrahydrofuran under a nitrogen atmosphere was treated over 15 minutes with a solution of 10.0 ml (10.2 g; 0.067 mole) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 20 ml of tetrahydrofuran. The mixture was stirred at room temperature for 16 hours, then added to 450 g of ice/water. Acidification with 6.0N hydrochloric acid precipitated the crude naphthalene ester product. The solid was filtered, washed with water, and recrystallized from aqueous methanol to yield 5.1 g (67% yield) of the final product, mp 109°-111°. This material was identical with that prepared by the procedure described in Example 11.

Workup

  1. customAcidification with 6.0N hydrochloric acid precipitated the crude naphthalene ester product
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-9d69bf3a04044b388d423dcf70b25191
Source dataset
uspto-grants-1988_08
Patent number
US04767776

Reaction notes

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