Acetic Anhydride → 3-[2,4-Bis(dimethylamino)phenyl]-3-(1,2-dimethyl-3-indolyl)-4,5,6,7-tetrachlorophthalide

HRID 1703226Notes

Reaction equation

HRID 1703226 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([C:13]2[C:21]([Cl:22])=[C:20]([Cl:23])[C:19]([Cl:24])=[C:18]([Cl:25])[C:14]=2[C:15]([OH:17])=O)=[O:12])=[C:3]1[CH3:26].[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.[OH-].[NH4+]>Cl>[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:11]1([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[C:3]=2[CH3:26])[C:13]2[C:14](=[C:18]([Cl:25])[C:19]([Cl:24])=[C:20]([Cl:23])[C:21]=2[Cl:22])[C:15](=[O:17])[O:12]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 205235362-[(1,2-Dimethyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid

Product 1

HCID 205235653-[2,4-Bis(dimethylamino)phenyl]-3-(1,2-dimethyl-3-indolyl)-4,5,6,7-tetrachlorophthalide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1.55 g (0.0036 mole) of 2-[(1,2-dimethyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid prepared in a manner similar to part A of Example 2, 0.58 g (0.0035 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and ten ml of acetic anhydride was heated to reflux for approximately one hour. After cooling to room temperature, the reaction mixture was poured into 20 ml of 10 percent hydrochloric acid and the mixture then rendered alkaline by the addition of concentrated ammonium hydroxide. The purple solid which separated was collected by filtration, dried, and recrystallized twice from isopropyl acetate to obtain 3-[2,4-bis(dimethylamino)phenyl]-3-(1,2-dimethyl-3-indolyl)-4,5,6,7-tetrachlorophthalide (Formula III: R0 =R1 =R2 =R3 =Cl; R=R5 =R6 =CH3 ; R4 =N(CH3)2 ; Y1 =H) which decomposed at 228°-229° C. The mass spectrum showed an m/e at 575 (M+, 4 Cl). A toluene solution of the product spotted on silica gel developed an intense purple-colored image.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for approximately one hour
  3. customThe purple solid which separated
  4. filtrationwas collected by filtration
  5. customdried
  6. customrecrystallized twice from isopropyl acetate

Sources & evidence

ORD record
ord-66e49755e88a4666b5c7320479fa07f2
Source dataset
uspto-grants-1982_09
Patent number
US04351768

Reaction notes

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