Hydrochloric Acid → 2',4',6'-Triiodo-3',5'-bis(ethyl)-3-nitrobiphenyl-4-carboxylic acid

HRID 1976511Notes

Reaction equation

HRID 1976511 reaction equation
[I:1][C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([I:10])[C:5]([C:11](=O)[CH3:12])=[C:4]([I:14])[C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[C:17]([N+:24]([O-:26])=[O:25])[CH:16]=1.Cl>>[I:1][C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([I:10])[C:5]([CH2:11][CH3:12])=[C:4]([I:14])[C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[C:17]([N+:24]([O-:26])=[O:25])[CH:16]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 223419922',4',6'-Triiodo-3'-ethyl-5'-acetyl-3-nitrobiphenyl-4-carboxylic acid

Product 1

HCID 223420052',4',6'-Triiodo-3',5'-bis(ethyl)-3-nitrobiphenyl-4-carboxylic acid

Procedure

Freidel-Crafts acylation is performed on 2′,4′,6′-triiodo-3′-ethyl-3-nitrobiphenyl-4-carboxylic acid (13) in the presence of AlCl3 and CH3COCl to yield 2′,4′,6′-triiodo-3′-ethyl-5′-acetyl-3-nitrobiphenyl-4-carboxylic acid (17). 2′,4′,6′-triiodo-3′-ethyl-5′-acetyl-3-nitrobiphenyl-4-carboxylic acid (17) is then reacted with a zinc mercury amalgam and hydrochloric acid and heated to yield 2′,4′,6′-triiodo-3′,5′-bis(ethyl)-3-nitrobiphenyl-4-carboxylic acid (18)

Workup

  1. temperatureheated

Sources & evidence

ORD record
ord-92d09aa078ed4cfaa75f40464c50a149
Source dataset
uspto-grants-2001_05
Patent number
US06226352B1

Reaction notes

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