4-Methoxyphenylacetaldehyde → HCID 12390944, compound

HRID 2419086Notes

Reaction equation

HRID 2419086 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]=O)=[CH:5][CH:4]=1.[BrH:12].[NH2:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:25])[C:20]=2[OH:24])[C:15]1=[O:26]>C(O)C.[Pd]>[BrH:12].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][NH:13][CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([OH:25])[C:20]=3[OH:24])[C:15]2=[O:26])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 797824-MethoxyphenylacetaldehydeHCID 12353616HCID 12353616, compound

Product 1

HCID 12390944HCID 12390944, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In 1000 volume parts of ethanol is dissolved 10 parts of 2-amino-5,6-dihydroxy-3,4-dihydro-1(2H)-naphthalenone hydrobromide, followed by the addition of 100 parts of 4-methoxyphenylacetaldehyde. Using palladium-on-carbon as a catalyst, catalytic reduction is carried out at ordinary temperature and pressure. When a stoichiometric amount of hydrogen has been absorbed, the reaction mixture is filtered and the filtrate is concentrated under reduced pressure. The procedure yields 8 parts of 2-(4-methoxyphenethyl)amino-5,6-dihydroxy-3,4-dihydro-1(2H)-naphthalenone hydrobromide as colorless crystals melting at 198°-203° C.

Workup

  1. customWhen a stoichiometric amount of hydrogen has been absorbed
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-157570ee09ec4735b76f65e060a17eda
Source dataset
uspto-grants-1978_08
Patent number
US04104402

Reaction notes

Loading…