Anthranilic Acid → Benzoic acid, 2,2'-[(9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)diimino]bis-

HRID 2198796Notes

Reaction equation

Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:19]([OH:28])(=[O:27])[C:20]1[C:21](=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH2:22].[O-2:29].[Mg+2].[OH-:31].[K+].S(=O)(=O)(O)O>O.C(O)C(C)C>[C:19]([C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH:22][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH:22][C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[C:19]([OH:31])=[O:29])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1)([OH:28])=[O:27]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1,5-dichloroanthraquinone (12.0 g.), anthranilic acid (37.0 g.), magnesium oxide (3.2 g.), cupric oxide (0.8 g.), potassium hydroxide (15.0 g.), water (60 ml), and isobutyl alcohol (6 ml) was heated in an autoclave at 150° C. for 20 hrs. The reaction mixture was diluted with 500 ml water, acidified with sulfuric acid (15 ml), and then heated to 80°-85° C. with stirring. After cooling, the product was collected by filtration and washed with water. The dried product was purified by recrystallization from N-methyl-2-pyrrolidinone. This product is one of the most preferred comonomers.

Workup

temperatureheated to 80°-85° C.
temperatureAfter cooling
filtrationthe product was collected by filtration
washwashed with water
customThe dried product was purified by recrystallization from N-methyl-2-pyrrolidinone

Sources & evidence

ORD record: ord-3430e0f94aaf4c9b979f293fa61a2cb0
Source dataset: uspto-grants-1982_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04359570

Reaction notes

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