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

HRID 1413873Notes

Reaction equation

HRID 1413873 reaction equation
[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].[CH3:28][N:29]([CH3:39])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([N:36]([CH3:38])[CH3:37])[CH:31]=1.C(OC(=O)C)(=O)C>C1C=CC=CC=1>[CH3:37][N:36]([CH3:38])[C:32]1[CH:31]=[C:30]([N:29]([CH3:39])[CH3:28])[CH:35]=[CH:34][C:33]=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:18])[O:17]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 197638051-Ethyl-2-methyl-3-(2-carboxy-3,4,5,6-tetrachlorobenzoyl)indole

Product 1

HCID 205235643-[2,4-Bis(dimethylamino)-phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalideYield 12.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred mixture of 8.86 g of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid, prepared as described in part A above, 4.0 g of N,N,N',N'-tetramethyl-m-phenylenediamine, and 10.0 ml of acetic anhydride was heated at reflux for a period of three hours. The reaction was then allowed to cool to room temperature, and the tan precipitate which formed was filtered and washed with isopropanol. The material thus obtained was dissolved in 500 ml of benzene and the resulting solution extracted with 70 ml of 10 percent aqueous sodium hydroxide. The benzene solution was filtered and evaporated to dryness at ambient temperature yielding 1.5 g of 3-[2,4-bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-4,5,6,7-tetrachlorophthalide (Formula III: R0 =R1 =R2 =R3 =Cl; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =CH2CH3 ; Y1 =H), a white solid which melted with decomposition at 227°-229° C. A significant infrared maximum occurred at 1770 cm-1 (C=O; s). The nuclear magnetic resonance spectrum was in complete agreement with the assigned structure. A benzene solution of this product spotted on silica gel developed an intense purple color.

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux for a period of three hours
  4. customthe tan precipitate which formed
  5. filtrationwas filtered
  6. washwashed with isopropanol
  7. customThe material thus obtained
  8. extractionthe resulting solution extracted with 70 ml of 10 percent aqueous sodium hydroxide
  9. filtrationThe benzene solution was filtered
  10. customevaporated to dryness at ambient temperature

Sources & evidence

ORD record
ord-7ed643df6ec14586bcc454979ba16013
Source dataset
uspto-grants-1981_02
Patent number
US04251446

Reaction notes

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