Acetic Anhydride → HCID 20268295, compound

HRID 1449082Notes

Reaction equation

HRID 1449082 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][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=O)=[C:4]1[CH3:23])[CH3:2].[CH3:24][N:25]([CH3:35])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N:32]([CH3:34])[CH3:33])[CH:27]=1.C(OC(=O)C)(=O)C>C(O)C>[CH3:33][N:32]([CH3:34])[C:28]1[CH:27]=[C:26]([N:25]([CH3:35])[CH3:24])[CH:31]=[CH:30][C:29]=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[CH3:23])[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16](=[O:18])[O:17]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 3084978Benzoic acid, 2-[(1-ethyl-2-methyl-1H-indol-3-yl)carbonyl]-

Product 1

HCID 20268295HCID 20268295, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a procedure similar to that described above in part B of this example, 12.28 g (0.04 mole) of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]benzoic acid, prepared as described in part A above, 8.57 g (0.05 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and 6.0 ml of acetic anhydride were interacted with stirring at room temperature overnight. The reaction mixture was then diluted with 13.0 ml of ethanol and the precipitate which separated was filtered and washed with 6.0 ml of ethanol. The filter cake was then reslurried in 30 ml of methanol, filtered and washed successively with methanol and diethylether. The material was dried in vacuo to obtain 15.8 g of 3-[2,4-bis(dimethylamino)phenyl]3-(1-ethyl-2-methyl-3-indolyl)phthalide (Formula III: R°=R1 =R2 =R3 =Y1 =H; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =CH2CH3), a white crystalline solid which melted at 218° -222° C. The infrared spectrum was consistent with the structure. A benzene solution of the above product developed in intense grape-red color when streaked on a phenolic resin coated paper.

Workup

  1. customprepared
  2. customthe precipitate which separated
  3. filtrationwas filtered
  4. washwashed with 6.0 ml of ethanol
  5. filtrationfiltered
  6. washwashed successively with methanol and diethylether
  7. customThe material was dried in vacuo

Sources & evidence

ORD record
ord-b101c8026bc4499990d0653b5b9165e9
Source dataset
uspto-grants-1980_02
Patent number
US04189171

Reaction notes

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