Sulfuric Acid → 1-(beta-Carboxyethylamino)anthraquinone

HRID 2083653Notes

Reaction equation

[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[NH2:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:22])[C:11]=2[CH:10]=[CH:9][CH:8]=1.B(O)(O)O.S(=O)(=O)(O)O>>[C:1]([CH2:2][CH2:3][NH:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:22])[C:11]=2[CH:10]=[CH:9][CH:8]=1)([OH:5])=[O:4]

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 6581Acrylic Acid

HCID 67101-Aminoanthraquinone

HCID 7628Boric Acid

Product 1

HCID 106852681-(beta-Carboxyethylamino)anthraquinoneYield 91.5%

Procedure

15 Parts of acrylic acid are gradually added to a mixture of 22.3 parts of 1-aminoanthraquinone, 6.2 parts of boric acid and 120 parts of 100% sulphuric acid at 30°-35° C, and the mixture is then stirred for 12 hours at 90° - 95° C. The reaction mixture is then processed as described in Example 1 to give 27 parts (91.5%) of 1-(β-carboxyethylamino)anthraquinone.

Sources & evidence

ORD record: ord-24f28eb661134ca8a4a0a2924ad219b3
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04086252

Reaction notes

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