Diphenylamine → Acetic Anhydride

HRID 1388980Notes

Reaction equation

HRID 1388980 reaction equation
C(N1C2C(=CC=CC=2)C(C(C2C=NC=C[C:19]=2[C:20]([OH:22])=[O:21])=O)=C1C)C.[CH2:24]([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35]([C:37]2[CH:42]=[CH:41][N:40]=[CH:39][C:38]=2[C:43]([OH:45])=[O:44])=[O:36])=[C:27]1[CH3:46])[CH3:25].[C:47]1([NH:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>N1C=CC=CC=1>[C:35]([O:22][C:20](=[O:21])[CH3:19])(=[O:36])[CH3:28].[CH2:24]([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35]2([N:53]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:37]3[CH:42]=[CH:41][N:40]=[CH:39][C:38]=3[C:43](=[O:45])[O:44]2)=[C:27]1[CH3:46])[CH3:25]

Participants

6

Reactant 3

HCID 11487DiphenylamineHCID 20534275HCID 20534275, compoundHCID 20534282HCID 20534282, compound

Product 2

HCID 7918Acetic AnhydrideHCID 20534283HCID 20534283, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following a procedure similar to that described in Example 3 but employing 1.6 g. of an isomer mixture comprising 3-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-4-pyridinecarboxylic acid and 4-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-3-pyridinecarboxylic acid, 0.9 g. of diphenylamine, 0.5 ml. of pyridine and 6 ml. of acetic anhydride there was obtained 1-(1-ethyl-2-methyl-3-indolyl)-1-(diphenylamino)furo[3,4-c]pyridine-3(1H)-one as a viscous oil. A toluene solution of the product contacted with acidic clay or phenolic resin developed an orange image.

Sources & evidence

ORD record
ord-920756fe9b024854baa1d3512367edb7
Source dataset
uspto-grants-1981_01
Patent number
US04243250

Reaction notes

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