1,3-Benzenediamine, N1,N1,N3,N3-tetramethyl- → 3-[2,4-Bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-nitrophthalide

HRID 1660270노트

반응식

HRID 1660270 반응식
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:14]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=O)=[C:4]1[CH3:26])[CH3:2].[CH3:27][N:28]([CH3:38])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N:35]([CH3:37])[CH3:36])[CH:30]=1>C(OC(=O)C)(=O)C>[CH3:36][N:35]([CH3:37])[C:31]1[CH:30]=[C:29]([N:28]([CH3:38])[CH3:27])[CH:34]=[CH:33][C:32]=1[C:12]1([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:3]([CH2:1][CH3:2])[C:4]=2[CH3:26])[C:14]2[C:15](=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[C:16](=[O:18])[O:17]1

참가 물질

4

반응물 2

HCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 205235612-(1-Ethyl-2-methyl-1H-indole-3-carbonyl)-5-nitrobenzoic acid

생성물 1

HCID 205235443-[2,4-Bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-nitrophthalide수율 76.2%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

반응 조건

온도
90 °C

실험 절차

A mixture of 3.68 g (0.01 mole) of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-5-nitrobenzoic acid, prepared as described in part A above, and 2.0 g (0.012 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine in 10.0 ml of acetic anhydride was heated at 90° C. for one hour and then allowed to cool to 25° C. The solid which separated was collected by filtration, washed with diethylether and dried to obtain 3.8 g of 3-[2,4-bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-nitrophthalide (Formula III: Ro =R1 =R3 =Y1 =H; R2 =NO2 ; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =CH2CH3) as an orange solid which melted over the range 185°-187° C. The nuclear magnetic resonance spectrum was in accord with the assigned structure. A benzene solution of this product developed a black-purple color when spotted on silica gel.

후처리

  1. customprepared
  2. temperatureto cool to 25° C
  3. customThe solid which separated
  4. filtrationwas collected by filtration
  5. washwashed with diethylether
  6. customdried

출처 및 근거

ORD 기록
ord-a8f3ccafdf1a4326b298a60aae5e8dc8
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04307018

반응 노트

불러오는 중…