Chloral → HCID 20485999, compound

HRID 647362Notes

Reaction equation

HRID 647362 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:13]([OH:17])[CH2:14]NC)[CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10].C[O:19]C1C=CC=C(OC)C=1O.O=CC(Cl)(Cl)Cl.COC1C=C(C(O)C(Cl)(Cl)Cl)C=C(OC)C=1O>>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]([CH:14]=[O:19])=[O:17])[CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10]

Participants

5

Reactant 4

HCID 6407ChloralHCID 70412,6-DimethoxyphenolHCID 13050550HCID 13050550, compoundHCID 698548804-[1-Hydroxy-2-(methylamino)ethyl]-2,6-dimethoxyphenol--hydrogen chloride (1/1)

Product 1

HCID 20485999HCID 20485999, compound

Procedure

A process for preparing 1-(3,5-dimethoxy-4-hydroxy phenyl)-2-(N-methylamino) ethanol hydrochloride is described by reacting 2,6-dimethoxyphenol with anhydrous chloral in the presence of a catalyst, hydrolyzing 1-(3,5-dimethoxy-4-hydroxyphenyl)2,2,2-trichloro ethanol and subsequently isolating the 3,5-dimethoxy-4-hydroxyphenyl glyoxal thus obtained; finally, this compound, in the form of the bisulfite, is directly converted to the desired product by amination with methylamine in the presence of hydrogen with a hydrogenation catalyst and the final product is converted into the hydrochloride.

Sources & evidence

ORD record
ord-e74d55d166fb463b8b530b62210df130
Source dataset
uspto-grants-1983_10
Patent number
US04408074

Reaction notes

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