Benzoic Acid → 37969-58-7

HRID 1164543Notes

Reaction equation

HRID 1164543 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:20])=[C:15]([O:18]C)[CH:16]=3)[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.O.O.O.[I-].[Li+].C(O)(=O)C1C=CC=CC=1>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:20])=[C:15]([OH:18])[CH:16]=3)[CH2:11][CH2:10][NH:9]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 12821122HCID 12821122, compoundHCID 23688288Lithium iodide--water (1/1/3)

Product 1

HCID 2051125237969-58-7

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(4-chlorophenoxy)methyl-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline (100 mg), lithium iodide trihydrate (150 mg) and benzoic acid (38 mg) was heated in an oil bath of 200° to 210° C. for 0.5 hour. After the reaction, the precipitated solid was dissolved in methanol absorbed with hydrogen chloride, and then insoluble material was filtered off. The filtrate was concentrated, and to the residue was added a small amount of ether, and the mixture was allowed to stand. The precipitated crystals were collected by filtration, and dried to give 1-(4-chlorophenoxy)methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride, mp 226° C. The product was identified with a sample by I.R. spectrum and N.M.R. spectrum.

Workup

  1. temperaturewas heated in an oil bath of 200° to 210° C. for 0.5 hour
  2. customAfter the reaction
  3. customabsorbed with hydrogen chloride
  4. filtrationinsoluble material was filtered off
  5. concentrationThe filtrate was concentrated
  6. additionto the residue was added a small amount of ether
  7. filtrationThe precipitated crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-3d573704b9d24859bc0c00f851f80e38
Source dataset
uspto-grants-1983_01
Patent number
US04370332

Reaction notes

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