Ammonia → 5-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

HRID 2166364노트

반응식

HRID 2166364 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([O:22][C:23]1[CH:28]=[CH:27][C:26](N)=[CH:25][CH:24]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].F[B-](F)(F)F.[H+].N([O-])=O.[Na+].P(P(O)(O)=O)(O)(O)=O.N>O.[Cu-]=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

참가 물질

8

반응물 5

HCID 222AmmoniaHCID 24536Hypophosphoric acidHCID 28118Tetrafluoroboric acidHCID 138000665(-4-Aminophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl esterHCID 23668193Sodium Nitrite

생성물 1

HCID 138000715-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester수율 57.4%

시약·촉매·용매 2

HCID 178419072HCID 178419072, 화합물촉매HCID 962Water용매3회

반응 조건

온도
0 °C

실험 절차

978 mg of 5(-4-aminophenoxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester is suspended in 2 ml of water and 10 ml of a 50% tetrafluoroboric acid. After cooling to 0° C., it is mixed drop by drop with a solution of 224 mg of sodium nitrite in 2 ml of water and stirred at 0° C. for 1/2 hour. Then it is mixed at the same temperature with a 60% hypophosphoric acid and 150 mg of copper(I) oxide, diluted with 10 ml of water and afterwards heated for 1/2 hour on the steam bath. After adjustment of the pH to 8 with soda and addition of ammonia, it is extracted with ethyl acetate. The ethyl acetate phase is evaporated and the residue chromatographed over silica gel with acetone: hexane=1:1 as eluant. 540 mg (57% of theory) of 5-phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester with a melting point of 174°-176° C. is obtained.

후처리

  1. temperatureafterwards heated for 1/2 hour on the steam bath
  2. extractionis extracted with ethyl acetate
  3. customThe ethyl acetate phase is evaporated
  4. customthe residue chromatographed over silica gel with acetone

출처 및 근거

ORD 기록
ord-0929175f96b44247a1c5568ebdec212e
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04945090

반응 노트

불러오는 중…