Diphenylamine → Acetic Anhydride
Reaction equation
[CH2:1]([N:3]([CH2:22][CH3:23])[C:4]1[CH:20]=[CH:19][C:7]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[C:16]([OH:18])=[O:17])=O)=[C:6]([CH3:21])[CH:5]=1)[CH3:2].[CH2:24]([N:26]([CH2:45][CH3:46])[C:27]1[CH:43]=[CH:42][C:30]([C:31]([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][C:34]=2[C:39]([OH:41])=[O:40])=[O:32])=[C:29]([CH3:44])[CH:28]=1)[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>>[C:31]([O:18][C:16](=[O:17])[CH3:15])(=[O:32])[CH3:30].[CH2:1]([N:3]([CH2:22][CH3:23])[C:4]1[CH:20]=[CH:19][C:7]([C:8]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:10]3[CH:11]=[N:12][CH:13]=[CH:14][C:15]=3[C:16](=[O:18])[O:17]2)=[C:6]([CH3:21])[CH:5]=1)[CH3:2].[CH2:45]([N:26]([CH2:24][CH3:25])[C:27]1[CH:43]=[CH:42][C:30]([C:31]2([N:53]([C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:33]3[CH:38]=[CH:37][N:36]=[CH:35][C:34]=3[C:39](=[O:40])[O:41]2)=[C:29]([CH3:44])[CH:28]=1)[CH3:46]Participants
6
Procedure
Following a procedure similar to that described in Example 3 but employing 1.6 g. of an isomer mixture comprising 3-[4-(diethylamino)-2-methylbenzoyl]-4-pyridinecarboxylic acid and 4-[4-(diethylamino)-2-methylbenzoyl]-3-pyridinecarboxylic acid, 0.9 g. of diphenylamine and 6 ml. of acetic anhydride there was obtained an isomer mixture comprising 3-[4-(diethylamino)-2-methylphenyl]-3-(diphenylamino)furo[3,4-c]pyridine-1(3H)-one and 1-[4-(diethylamino)-2-methylphenyl]-1-(diphenylamino)furo[3,4-c]pyridine-3(1H)-one. A toluene solution of the product contacted with acidic clay or phenolic resin developed a red-grape image.
Sources & evidence
- ORD record
- ord-cfa80065610f44eca3b1b32913bbadc0
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04243250
Reaction notes
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