Sodium Hydroxide → HCID 20063315, compound

HRID 1084430Notes

Reaction equation

HRID 1084430 reaction equation
[OH:1][CH:2]([CH2:9][CH:10]([OH:31])/[CH:11]=[CH:12]/[C:13]1[N:14]([CH3:30])[C:15](=[O:29])[C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[Na+]>CO.O>[OH:1][CH:2]([CH2:9][CH:10]([OH:31])/[CH:11]=[CH:12]/[C:13]1[N:14]([CH3:30])[C:15](=[O:29])[C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86744697HCID 86744697, compound

Product 1

HCID 20063315HCID 20063315, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl (E)-3,5-dihydroxy-7-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)-hept-6-enoate (0.35 g; prepared as described in Example 1) in methanol (15 ml) was cooled to 10° C. and treated with a solution of sodium hydroxide (0.17 g) in water (10 ml) dropwise during 10 minutes. The reaction mixture was warmed to room temperature, stirred for one hour and evaporated to dryness, and the residual solid, which was crude sodium (E)-3,5-dihydroxy-7-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)hept-6-enoate, was dissolved in water (50 ml). The aqueous solution was washed with diethyl ether (20 ml) and acidified to pH 5 by treatment with glacial acetic acid. The resulting yellow solid was filtered off and washed well with water, to give (E)-3,5-dihydroxy-7-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)hept-6-enoic acid (0.10 g), m.p. 170° C. [Elemental analysis: C, 70.0; H, 5.92; N, 3.37%; calculated: C, 70.2; H, 5.89; N, 3.56%].

Workup

  1. customevaporated to dryness
  2. dissolutionwas dissolved in water (50 ml)
  3. washThe aqueous solution was washed with diethyl ether (20 ml)
  4. filtrationThe resulting yellow solid was filtered off
  5. washwashed well with water

Sources & evidence

ORD record
ord-f0d1a63b685f48aaaf966ea825b60a40
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

Loading…