Nitric Acid → 4-Chloro-9,10-dioxo-9,10-dihydroanthracene-1-carboxylic acid

HRID 508595Notes

Reaction equation

Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5](C)=[CH:4][CH:3]=1.[N+]([O-])(O)=[O:20].[CH:23]([Cl:26])(Cl)Cl.[OH2:27]>>[Cl:26][C:23]1[C:5]2[C:4](=[O:27])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:15]([C:14]([OH:20])=[O:16])=[CH:2][CH:3]=1

Participants

Reactant 4

HCID 944Nitric Acid

HCID 962Water2×

HCID 6212Chloroform

HCID 3441301-Chloro-4-methylanthraquinone

Product 1

HCID 2355754-Chloro-9,10-dioxo-9,10-dihydroanthracene-1-carboxylic acidYield 61%

Procedure

A suspension of 1-chloro-4-methylanthraquinone (6 g, 23.37 mmol) in the mixture of 12 ml 65% nitric acid and 24 ml of water is heated in the pressure reactor with teflon lining at 200° C. for 6 hours. The reaction mixture, after cooling, is diluted with water and the resulting precipitate is filtrated. The obtained crude acid is treated with chloroform, filtered and next crystallized with ethyl acetate to give 4.1 g (61% yield) of 4-chloroanthra quinone 1-carboxylic acid.

Workup

temperatureThe reaction mixture, after cooling
filtrationthe resulting precipitate is filtrated
customThe obtained crude acid
filtrationfiltered
customnext crystallized with ethyl acetate

Sources & evidence

ORD record: ord-ba3b25c8a5a54a6bba880f8ff334e757
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096536B2

Reaction notes

Loading…