Oxalic Acid → 5-(2-Hydroxy-5-nitro-benzyl)-6-methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine

HRID 261069

Reaction equation

HRID 261069 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][C:5]2[CH:8]=[CH:9][S:10][C:4]=2[CH2:3]1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([O-:13])=[O:12].O1CCOC[CH2:22]1.C(O)(=O)C(O)=O>C(O)C>[OH:20][C:17]1[CH:18]=[CH:19][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][C:16]=1[CH2:22][N:7]1[CH:2]([CH3:1])[CH2:3][C:4]2[S:10][CH:9]=[CH:8][C:5]=2[CH2:6]1

Participants

7

Reactant 5

HCID 971Oxalic AcidHCID 9804-NitrophenolHCID 312751,4-DioxaneHCID 203219916-Methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridineHCID 178486302HCID 178486302, compound

Product 1

HCID 203960375-(2-Hydroxy-5-nitro-benzyl)-6-methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridineYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (6.3 g; 41 mmoles), p-nitro-phenol (5.7 g; 41 mmoles), polyoxymethylene (2.5 g; 83 mmoles) and dioxan (50 cc) is stirred at 80° C. during 4 hours. After concentration in vacuo, the residue is dissolved in ether and then treated with 0.5 equivalent oxalic acid in ethanol solution. The resulting semi-oxalate is filtered, washed with boiling methanol-water (1:3), filtered again and dried (M.p.= 214° C.; yield: 27%).

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue is dissolved in ether
  3. filtrationThe resulting semi-oxalate is filtered
  4. washwashed with boiling methanol-water (1:3)
  5. filtrationfiltered again
  6. customdried (M.p.= 214° C.; yield: 27%)

Sources & evidence

ORD record
ord-3d13a2696d7346819c9049d84c7ccdfa
Source dataset
uspto-grants-1979_08
Patent number
US04163852

Linked notes

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