N-(3-Methylphenyl)aniline → Acetic Anhydride

HRID 1157022Notes

Reaction equation

HRID 1157022 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[C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:13])=[C:4]1[CH3:23])[CH3:2].C(N1C2[C:29](=[CH:30][CH:31]=CC=2)[C:28]([C:35](C2C(C(O)=O)=NC=CC=2)=[O:36])=[C:27]1[CH3:46])C.C1([NH:53][C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([CH3:60])[CH:55]=2)C=CC=CC=1>N1C=CC=CC=1>[C:35]([O:22][C:20](=[O:21])[CH3:19])(=[O:36])[CH3:28].[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2([NH:53][C:54]3[CH:59]=[CH:58][CH:57]=[C:56]([C:60]4[CH:46]=[CH:27][CH:28]=[CH:29][C:30]=4[CH3:31])[CH:55]=3)[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:19]3[C:20](=[O:21])[O:13]2)=[C:4]1[CH3:23])[CH3:2]

Participants

6

Reactant 3

HCID 14569N-(3-Methylphenyl)anilineHCID 1090822-Pyridinecarboxylic acid, 3-[(1-ethyl-2-methyl-1H-indol-3-yl)carbonyl]-HCID 1123443-Pyridinecarboxylic acid, 2-((1-ethyl-2-methyl-1H-indol-3-yl)carbonyl)-

Product 2

HCID 7918Acetic AnhydrideHCID 70544473HCID 70544473, 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 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-3-pyridinecarboxylic acid and 3-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-2-pyridinecarboxylic acid, 0.95 g. of N-phenyl-m-toluidine, 0.5 ml. of pyridine and 6 ml. of acetic anhydride there was obtained 7-(1-ethyl-2-methyl-3-indolyl)-7-(m-tolylphenylamino)furo[3,4-b]-pyridine-5(7H)-one as a yellow solid, m.p. 178°-190° C. (dec.). A toluene solution of the product contacted with acidic clay or phenolic resin developed an orange image.

Sources & evidence

ORD record
ord-ad446cdf3bf04052953e77aa7ff75e73
Source dataset
uspto-grants-1982_06
Patent number
US04337340

Reaction notes

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