Acetic Anhydride → 3-[2,4-Bis(diethylamino)phenyl]-3-(1-n-octyl-2-methyl-3-indolyl)phthalide

HRID 1703237Notes

Reaction equation

HRID 1703237 reaction equation
[CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]([C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([OH:24])=O)=[O:19])=[C:10]1[CH3:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:30]([N:32]([CH2:44][CH3:45])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])[CH:34]=1)[CH3:31].C(OC(=O)C)(=O)C>>[CH2:40]([N:39]([CH2:42][CH3:43])[C:35]1[CH:34]=[C:33]([N:32]([CH2:30][CH3:31])[CH2:44][CH3:45])[CH:38]=[CH:37][C:36]=1[C:18]1([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:10]=2[CH3:29])[C:20]2[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:22](=[O:24])[O:19]1)[CH3:41]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 19382815N~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamineHCID 197638022-(2-Methyl-1-octyl-1H-indole-3-carbonyl)benzoic acid

Product 1

HCID 205235523-[2,4-Bis(diethylamino)phenyl]-3-(1-n-octyl-2-methyl-3-indolyl)phthalide

Procedure

Proceeding in a manner similar to that described in part B of Example 5 above, 2.34 g (0.006 mole) of 2-[(1-n-octyl-2-methyl-3-indolyl)carbonyl]benzoic acid prepared according to Example 5, part A, and 2.40 g of N,N,N',N'-tetraethyl-m-phenylenediamine were interacted in the presence of 2.40 g of acetic anhydride to obtain 3-[2,4-bis(diethylamino)phenyl]-3-(1-n-octyl-2-methyl-3-indolyl)phthalide (Formula III: R0 =R1 =R2 =R3 =Y1 =H; R=CH2CH3 ; R4 =N(CH2CH3)2 ; R5 =CH3 ; R6 =(CH2)7CH3) as a tar-like semisolid. A toluene solution of this material developed a purple color when spotted on silica gel.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-d60d6d178399431b9cfd3261d91c7292
Source dataset
uspto-grants-1982_09
Patent number
US04351768

Reaction notes

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