Nitrobenzene → Palladium tetraphenylporphyrin

HRID 2285453Notes

Reaction equation

[N+](C1C=CC=CC=1)([O-])=O.[CH:10]1[CH:11]=[CH:12][C:13]([C:16]2[C:17]3[NH:21][C:20]([C:22]([C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)=[C:23]4[CH:51]=[CH:50][C:25](=[C:26]([C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=5)[C:27]5[CH:43]=[CH:42][C:29](=[C:30]([C:36]6[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=6)[C:31]6[CH:32]=[CH:33][C:34]=2[N:35]=6)[N:28]=5)[NH:24]4)=[CH:19][CH:18]=3)=[CH:14][CH:15]=1.[Pd:58].[C]=O>ClC1C=CC=CC=1Cl>[C:52]1([C:22]2[C:20]3[NH:21][C:17](=[CH:18][CH:19]=3)[C:16]([C:13]3[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=3)=[C:34]3[N:35]=[C:31]([CH:32]=[CH:33]3)[C:30]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[C:29]3[NH:28][C:27]([CH:43]=[CH:42]3)=[C:26]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:25]3=[N:24][C:23]=2[CH:51]=[CH:50]3)[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.[Pd:58]

Participants

Conditions

Temperature: 240 °C

Procedure

10 g of nitrobenzene, 0.6 g of tetraphenylporphyrin and 0.1 g of palladium black are placed in the autoclave and the total volume is then brought to 100 ml by means of orthodichlorobenzene. The autoclave is scavenged with nitrogen, then 200 bars of carbon monoxide are introduced. After isolating the reactor and starting the stirring, it is heated at 240° C. for 3 and three-quarter hours, thus limiting voluntarily the progress of the reaction. After cooling analysis shows that the O.C.R. of the nitrobenzene is 33.1%. The complex is purified by operating in the same way as in Example 10. Palladium tetraphenylporphyrin is thus obtained with a yield of 78%.

Workup

customAfter isolating the reactor
customthe progress of the reaction
temperatureAfter cooling analysis
customThe complex is purified

Sources & evidence

ORD record: ord-aff728bb9a16471c8983da603821d14a
Source dataset: uspto-grants-1982_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04323515

Reaction notes

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