1,3-Benzenediamine, N1,N1,N3,N3-tetramethyl- → HCID 20523575, compound

HRID 1413894Notes

Reaction equation

HRID 1413894 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([C:13]2[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])=O)=[C:3]1[CH3:25].[CH3:26][N:27]([CH3:37])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N:34]([CH3:36])[CH3:35])[CH:29]=1>C(OC(=O)C)(=O)C>[CH3:35][N:34]([CH3:36])[C:30]1[CH:29]=[C:28]([N:27]([CH3:37])[CH3:26])[CH:33]=[CH:32][C:31]=1[C:11]1([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[C:3]=2[CH3:25])[C:13]2[C:14](=[CH:18][C:19]([N:22]([CH3:24])[CH3:23])=[CH:20][CH:21]=2)[C:15](=[O:16])[O:17]1

Participants

4

Reactant 2

HCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 20523570HCID 20523570, compound

Product 1

HCID 20523575HCID 20523575, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 0.34 g (0.001 mole) of 2-[(1,2-dimethyl-3-indolyl)carbonyl]-5-dimethylaminobenzoic acid prepared as described in Example 1 of U.S. Pat. No. 3,540,910 was interacted with 0.16 g (0.001 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine in 5 ml of acetic anhydride in a similar manner to the procedure described in Example 1, part C hereinabove to obtain 3-[2,4-bis(dimethylamino)phenyl]-3-(1,2-dimethyl-3-indolyl)-6-dimethylaminophthalide (Formula III: R0 =R1 =R3 =Y1 =H; R2 =N(CH3)2 ; R=R5 =R6 =CH3 ; R4 =N(CH3)2) which melts over the range of 146°-152° C. A significant infrared absorption maximum appeared at 1760 cm-1 (C=O; s). A toluene solution of this product spotted on silica gel developed an intense grape-red-colored image.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-989b3bfd5c9047b2aef234a6501aba5e
Source dataset
uspto-grants-1981_02
Patent number
US04251446

Reaction notes

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