Acetic Anhydride → 3-[2,4-Bis(dimethylamino)phenyl]-3-(2,5-dimethyl-3-indolyl)phthalide

HRID 1703225Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])=O)=[CH:8][C:7]([CH3:22])=[CH:6][CH:5]=2.[CH3:23][N:24]([CH3:34])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N:31]([CH3:33])[CH3:32])[CH:26]=1.C(OC(=O)C)(=O)C>>[CH3:32][N:31]([CH3:33])[C:27]1[CH:26]=[C:25]([N:24]([CH3:34])[CH3:23])[CH:30]=[CH:29][C:28]=1[C:11]1([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:22])[CH:8]=3)[NH:3][C:2]=2[CH3:1])[C:13]2[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:15](=[O:16])[O:17]1

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-

HCID 204713512-(2,5-Dimethyl-1H-indole-3-carbonyl)benzoic acid

Product 1

HCID 205235553-[2,4-Bis(dimethylamino)phenyl]-3-(2,5-dimethyl-3-indolyl)phthalideYield 76.4%

Procedure

A mixture of 2.0 g (0.007 mole) of 2-[(2,5-dimethyl-3-indolyl)carbonyl]benzoic acid from part A above, 1.1 g (0.007 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and seven ml of acetic anhydride was interacted in a manner similar to that described in Example 3, part E above, to obtain 2.35 g of 3-[2,4-bis(dimethylamino)phenyl]-3-(2,5-dimethyl-3-indolyl)phthalide (Formula III: R0 =R1 =R2 =R3 =R6 =H; R=R5 =CH3 ; R4 =N(CH3)2 ; Y1 =CH3), a light purple solid melting over the range of 100°-125° C. The infrared showed a characteristic absorption maximum at 1760 cm-1 (C=O; s). A toluene solution of this product spotted on acid clay or phenolic resin developed an intense violet-colored image.

Sources & evidence

ORD record: ord-2666090d217646efb9936f1cc1e2af35
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04351768

Reaction notes

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