1,3-Benzenediamine, N1,N1,N3,N3-tetramethyl- → 3-[2,4-Bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-nitrophthalide

HRID 1703208Notes

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][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=O)=[C:4]1[CH3:26])[CH3:2].[CH3:27][N:28]([CH3:38])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N:35]([CH3:37])[CH3:36])[CH:30]=1>C(OC(=O)C)(=O)C>[CH3:36][N:35]([CH3:37])[C:31]1[CH:30]=[C:29]([N:28]([CH3:38])[CH3:27])[CH:34]=[CH:33][C:32]=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[CH3:26])[C:14]2[C:15](=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[C:16](=[O:18])[O:17]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3.68 g (0.01 mole) of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-5-nitrobenzoic acid, prepared as described in part A above, and 2.0 g (0.012 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine in 10.0 ml of acetic anhydride was heated at 90° C. for one hour and then allowed to cool to 25° C. The solid which separated was collected by filtration, washed with diethylether and dried to obtain 3.8 g of 3-[2,4-bis(dimethylamino)phenyl]-3-(1-ethyl-2-methyl-3-indolyl)-6-nitrophthalide (Formula III: R0 =R1 =R3 =Y1 =H; R2 =NO2 ; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =CH2CH3) as an orange solid which melted over the range 185°-187° C. The nuclear magnetic resonance spectrum was in accord with the assigned structure. A benzene solution of this product developed a black-purple color when spotted on silica gel.

Workup

customprepared
temperatureto cool to 25° C
customThe solid which separated
filtrationwas collected by filtration
washwashed with diethylether
customdried

Sources & evidence

ORD record: ord-1ad5250738d94f658e5bae4eb308918d
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04351768

Reaction notes

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