Pyrogallol → 9,10-Anthracenedione, 1-amino-4,5-dihydroxy-8-nitro-

HRID 2071672Notes

Reaction equation

ClC1C=CC=CC=1Cl.[N+:9]([C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[C:19]([OH:30])[CH:20]=[CH:21][C:22]=3[N+:27]([O-])=O)[C:17](=[O:31])[C:16]=2[C:15]([OH:32])=[CH:14][CH:13]=1)([O-:11])=[O:10].C1(C=CC=C(O)C=1O)O>CO>[NH2:27][C:22]1[C:23]2[C:24](=[O:26])[C:25]3[C:16](=[C:15]([OH:32])[CH:14]=[CH:13][C:12]=3[N+:9]([O-:11])=[O:10])[C:17](=[O:31])[C:18]=2[C:19]([OH:30])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 150 °C

Procedure

50 parts of o-dichlorobenzene, 8.25 parts of 1,8-dinitro-4,5-dihydroxyanthraquinone and 3.5 parts of pyrogallol are heated for 3 hours at 150° C while stirring. Then 3.5 parts of pyrogallol is introduced and the reaction mixture is heated for another 7 hours at 150° C. After the reaction mixture has been cooled to 60° C it is diluted with 120 parts of methanol and cooled to ambient temperature. The precipitated reduction product is suction filtered, washed with methanol and hot water and dried. 5.3 parts of 1-amino-8-nitro-4,5-dihydroxyanthraquinone is obtained.

Workup

temperatureAfter the reaction mixture has been cooled to 60° C it
temperaturecooled to ambient temperature
filtrationfiltered
washwashed with methanol and hot water
customdried

Sources & evidence

ORD record: ord-84855392ebc748cfbe6422be6c19a18e
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04048199

Reaction notes

Loading…