2-(3,4-Dichlorophenyl)-2-hydroxyacetic acid → N-[(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl) methyl]-3,4-dichloromandelamide

HRID 654238Notes

Reaction equation

HRID 654238 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH:5]([OH:9])[C:6]([OH:8])=O.[NH2:14][CH2:15][CH:16]1[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][C:20]([O:26][CH3:27])=[CH:21][CH:22]=2)[CH2:17]1>>[CH3:27][O:26][C:20]1[CH:19]=[C:18]2[C:23]([CH2:24][CH2:25][CH:16]([CH2:15][NH:14][C:6](=[O:8])[CH:5]([C:4]3[CH:10]=[CH:11][C:12]([Cl:13])=[C:2]([Cl:1])[CH:3]=3)[OH:9])[CH2:17]2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 2212752-(3,4-Dichlorophenyl)-2-hydroxyacetic acidHCID 15718600(7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanamine

Product 1

HCID 15718627N-[(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl) methyl]-3,4-dichloromandelamideYield 81.5%

Procedure

By following the procedure of Example 1(i) but starting from 3,4-dichloromandelic acid (3.1 g, 0.014 mol) and 2-aminomethyl-7-methoxy-1,2,3,4-tetrahydronaphthalene (2.67 g, 0.014 mol), N-[(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl) methyl]-3,4-dichloromandelamide (4.5 g) is obtained as an oily product characterised by the following IR absorption maxima 3380 (b): O--H, CON--H; and 1641: NHC=0 cm-1.

Sources & evidence

ORD record
ord-22ee088bbeaa479aadbdeaed4f272c76
Source dataset
uspto-grants-1992_07
Patent number
US05130339

Reaction notes

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