Water → 3-[2,4-Bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-acetamidophthalide

HRID 1449088Notes

Reaction equation

HRID 1449088 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[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:15]=2[C:16]([OH:18])=O)=[O:13])=[C:4]1[CH3:24])[CH3:2].[CH3:25][N:26]([CH3:36])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N:33]([CH3:35])[CH3:34])[CH:28]=1.O.[C:38](OC(=O)C)(=[O:40])[CH3:39]>>[CH3:34][N:33]([CH3:35])[C:29]1[CH:28]=[C:27]([N:26]([CH3:36])[CH3:25])[CH:32]=[CH:31][C:30]=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[CH3:24])[C:14]2[C:15](=[CH:19][C:20]([NH:23][C:38](=[O:40])[CH3:39])=[CH:21][CH:22]=2)[C:16](=[O:18])[O:13]1

Participants

5

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 205235662-[(1-Ethyl-2-methyl3-indolyl)carbonyl]-5-aminobenzoic acid

Product 1

HCID 205235433-[2,4-Bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-acetamidophthalide

Conditions

Temperature
50 °C

Procedure

A mixture of 3.22 g (0.01 mole) of 2-[(1-ethyl-2-methyl3-indolyl)carbonyl]-5-aminobenzoic acid, 118 g (0.01 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine in 10.0 ml of acetic anhydride was heated to 50° C. for one-half hour. After cooling to ambient temperature, 50 ml of water was added and the reaction mixture was filtered. The filtrate was rendered alkaline with dilute aqueous sodium hydroxide in the presence of 100 ml of toluene. The toluene layer was separated, dried and evaporated to obtain as tan crystals 3-[2,4-bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-acetamidophthalide (Formula III: R°=R1 =R3 =Y1 =H; R2 =NHCOCH3 ; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =CH2CH3) having a melting point of 204°-206° C. Infrared analyses showed maxima at 1733 cm-1 (C=O; s) and 1695 cm-1 (C=O; s). Nuclear magnetic resonance analsis was consistent with the structure. An acetone solution of the above compound developed an intense grape color when spotted on silica gel.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe reaction mixture was filtered
  3. customThe toluene layer was separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-d38bff8f74574894b4c859c79ad2d0ad
Source dataset
uspto-grants-1980_02
Patent number
US04189171

Reaction notes

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