Dimethylformamide → 9-Amino-7-chloro-3,4-dihydroacridin-1(2H)-one

HRID 2309444

반응식

HRID 2309444 반응식
CN(C)C=O.Cl.[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([NH:16][C:17]2[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH:18]=2)=[C:12]([CH:15]=1)[C:13]#[N:14].O=C1CCCC(NC2C=CC=CC=2C#N)=C1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[NH2:14][C:13]1[C:12]2[C:11]([N:16]=[C:17]3[C:18]=1[C:19](=[O:23])[CH2:20][CH2:21][CH2:22]3)=[CH:10][CH:9]=[C:8]([Cl:7])[CH:15]=2

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 184360Benzonitrile, 2-((3-oxo-1-cyclohexen-1-yl)amino)-HCID 200377145-Chloro-2-(3-oxocyclohexen-1-yl)aminobenzonitrile hydrochloride

생성물 1

HCID 137560579-Amino-7-chloro-3,4-dihydroacridin-1(2H)-one수율 4.3%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

In 5 liters of toluene were combined 200 ml of dimethylformamide, 180.71 g of 5-chloro-2-(3-oxocyclohexen-1-yl)aminobenzonitrile hydrochloride prepared in the same manner as the compounds of Examples 1 and 2, 176 g (2 eq) of milled K2CO3 and 3 g of cuprous chloride (CuCl). After 6 hours of reflux 3 g more of CuCl was added. After 12 hours of reflux 3 g more of CuCl was added. After overnight reflux the reaction mixture was evaporated and the residue extracted with dichloromethane via a Soxhlet extraction apparatus for 12 hours. The dichloromethane solution was evaporated to a solid. The solid was suspended in water and H2SO4 was added. The resultant salt which precipitated out was filtered and made basic with 10% NaOH. The solid was filtered and recrystallized twice from isopropanol/toluene to yield 6.84 g (4%) of a solid, melting point over 260° C.

후처리

  1. temperatureAfter overnight reflux the reaction mixture
  2. customwas evaporated
  3. extractionthe residue extracted with dichloromethane via a Soxhlet extraction apparatus for 12 hours
  4. customThe dichloromethane solution was evaporated to a solid
  5. additionH2SO4 was added
  6. customThe resultant salt which precipitated out
  7. filtrationwas filtered
  8. filtrationThe solid was filtered
  9. customrecrystallized twice from isopropanol/toluene

출처 및 근거

ORD 기록
ord-967cb771ab304006a9c67c268998579c
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04695573

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