N-(2-Chloroethyl)dibenzylamine → 3-(2-Dibenzylaminoethoxy)salicylic acid methyl ester

HRID 4546

Reaction equation

HRID 4546 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:5]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:19]([N:26]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:27][CH2:28]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[C:6]([O:10][CH2:28][CH2:27][N:26]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:7]=[CH:8][CH:9]=1)[OH:11]

Participants

5

Reactant 3

HCID 5820N-(2-Chloroethyl)dibenzylamineHCID 11430Potassium CarbonateHCID 75484Methyl 2,3-Dihydroxybenzoate

Product 1

HCID 539294463-(2-Dibenzylaminoethoxy)salicylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,3-dihydroxybenzoic acid methyl ester is reacted in the presence of potassium carbonate in acetonitrile with 1.1 equivalents of 1-dibenzylamino-2-chloroethane for 18 hours at 82°. The crude 3-(2-dibenzylaminoethoxy)salicyclic acid methyl ester obtained after working up is put to further use without further purification.

Sources & evidence

ORD record
ord-bdd53f2aa794405982b767a086f662bc
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Linked notes

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