1,3-Benzenediamine, N1,N1,N3,N3-tetramethyl- → HCID 20523540, compound

HRID 1449098Notes

Reaction equation

HRID 1449098 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][CH:7]=[CH:6][CH:5]=2.[CH3:22][N:23]([CH3:33])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]([CH3:32])[CH3:31])[CH:25]=1>C(OC(=O)C)(=O)C>[CH3:31][N:30]([CH3:32])[C:26]1[CH:25]=[C:24]([N:23]([CH3:33])[CH3:22])[CH:29]=[CH:28][C:27]=1[C:11]1([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][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:17])[O:16]1

Participants

4

Reactant 2

HCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 12248789Benzoic acid, 2-[(2-methyl-1H-indol-3-yl)carbonyl]-

Product 1

HCID 20523540HCID 20523540, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixturwe of 8.37 g (0.03 mole) of 2-[(2-methyl-3-indolyl)carbonyl]benzoic acid, prepared as described in part A above, 8.37 g (0.05 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and 10 ml of acetic anhydride was interacted at 50° C. as described in part B of Example 8 above to obtain 3-[2,4-bis(dimethylamino)phenyl]-3-(2-methyl-3-indolyl)phthalide (Formula III: R°=R1 =R2 =R3 =R6 =Y1 =H; R=R5 =CH3 ; R4 =N(CH3)2). After purification by slurrying in a benzene and ligroin mixture, the collected and dried product melted at 183°-186° C. The product had mass spectrum with a m/e peak at 425 (M+). Both the infrared and nuclear magnetic resonance spectra were consistent with this structure. A toluene solution of the product spotted on a phenolic resin coated paper developed an intense grape-colored image.

Workup

  1. customwas interacted at 50° C.

Sources & evidence

ORD record
ord-848c12cd615d4d38b45ef93f5b946cf2
Source dataset
uspto-grants-1980_02
Patent number
US04189171

Reaction notes

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