Acetic Anhydride → 3-[2-Acetamido-4-dimethylaminophenyl]-3-(1-ethyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalide

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[C:22]([Cl:23])=[C:21]([Cl:24])[C:20]([Cl:25])=[C:19]([Cl:26])[C:15]=2[C:16]([OH:18])=[O:17])=O)=[C:4]1[CH3:27])[CH3:2].[NH2:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[N:32]([CH3:34])[CH3:33].[C:38](OC(=O)C)(=[O:40])[CH3:39]>>[C:38]([NH:28][C:29]1[CH:30]=[C:31]([N:32]([CH3:34])[CH3:33])[CH:35]=[CH:36][C:37]=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[CH3:27])[C:14]2[C:15](=[C:19]([Cl:26])[C:20]([Cl:25])=[C:21]([Cl:24])[C:22]=2[Cl:23])[C:16](=[O:17])[O:18]1)(=[O:40])[CH3:39]

참가 물질

반응물 3

HCID 7918Acetic Anhydride

HCID 76084N,N-dimethyl-m-phenylenediamine

HCID 197638051-Ethyl-2-methyl-3-(2-carboxy-3,4,5,6-tetrachlorobenzoyl)indole

생성물 1

HCID 205235483-[2-Acetamido-4-dimethylaminophenyl]-3-(1-ethyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalide

실험 절차

Proceeding in a manner similar to that described in Example 13 above, 4.43 g (0.01 mole) of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid, prepared as described in Example 2, part A above, was interacted with 2.0 g (0.015 mole) of m-amino-N,N-dimethylaniline in the presence of ten ml of acetic anhydride to obtain 3-[2-acetamido-4-dimethylaminophenyl]-3-(1-ethyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalide (Formula III: R0 =R1 =R2 =R3 =Cl; R=R5 =CH3 ; ##STR31## R6 =CH2CH3 ; Y1 =H) which developed a blue-green color when spotted on silica gel in the form of a toluene solution.