Pyridine → Isopropyl 1-amino-4-bromoanthraquinone-2-carboxylate

HRID 359674Notes

Reaction equation

HRID 359674 reaction equation
[NH2:1][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]([Br:18])=[CH:4][C:3]=1[C:19]([OH:21])=[O:20].S(Cl)(Cl)=O.N1C=C[CH:29]=[CH:28][CH:27]=1.ClC1C=CC=CC=1Cl>C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1.ClC1C=CC=CC=1>[NH2:1][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]([Br:18])=[CH:4][C:3]=1[C:19]([O:21][CH:28]([CH3:29])[CH3:27])=[O:20]

Participants

8

Reactant 4

HCID 1049PyridineHCID 72391,2-DichlorobenzeneHCID 24386Thionyl ChlorideHCID 2715931-Amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Product 1

HCID 19800488Isopropyl 1-amino-4-bromoanthraquinone-2-carboxylate

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 7237O-XyleneSolventHCID 7964ChlorobenzeneSolvent

Procedure

The starting 1-amino-4-bromoanthraquinone-2-carboxylic acid is reacted with 1.5 to 3 molar equivalents of a chlorinating agent such as thionyl chloride at a temperature of 80 to 100° C. for a period of about 1 to 3 hours in the presence of 0.01 to 5 molar equivalents (based on the raw material) of pyridine in 3 to 7-fold weight an amount of an inert solvent such as orthodichlorobenzene, chlorobenzene, toluene or xylene so as to be converted into an acid chloride. After the excess chlorinating agent has been removed therefrom under reduced pressure, 1.5 to 5 molar equivalents of isopropyl alcohol is added thereto and esterification is then performed at 60 to 80° C. for 1 to 3 hours. Afterward, the product is allowed to stand, thereby obtaining crystals of isopropyl 1-amino-4-bromoanthraquinone-2-carboxylate.

Workup

  1. customAfter the excess chlorinating agent has been removed
  2. additionunder reduced pressure, 1.5 to 5 molar equivalents of isopropyl alcohol is added

Sources & evidence

ORD record
ord-5766164820754fc3be50fa4245b1695e
Source dataset
uspto-grants-1991_03
Patent number
US05002925

Reaction notes

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