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

HRID 1647015

반응식

HRID 1647015 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 1140Toluene용매HCID 7237O-Xylene용매HCID 7964Chlorobenzene용매

실험 절차

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 a 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.

후처리

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

출처 및 근거

ORD 기록
ord-6794cf50d8644b1f9d0bd07864d3b5a3
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05182395

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