HCID 178450622, compound → 21H,22H-Porphine

HRID 1018183Notes

Reaction equation

C(OC([C:8]1[C:9]2[NH:13][C:12]([C:14](C(OCCCC)=O)=[C:15]3[N:45]=[C:18]([C:19](C(OCCCC)=O)=[C:20]4[NH:37][C:23](=[C:24](C(OCCCC)=O)[C:25]5[CH:26]=[CH:27][C:28]=1[N:29]=5)[CH:22]=[CH:21]4)[CH:17]=[CH:16]3)=[CH:11][CH:10]=2)=O)CCC>CN(C=O)C>[C:9]12[CH:8]=[C:28]3[N:29]=[C:25]([CH:26]=[CH:27]3)[CH:24]=[C:23]3[NH:37][C:20]([CH:21]=[CH:22]3)=[CH:19][C:18]3=[N:45][C:15]([CH:16]=[CH:17]3)=[CH:14][C:12]([NH:13]1)=[CH:11][CH:10]=2

Participants

Conditions

Temperature: 145 °C

Procedure

A solution of porphyrin 40 (355 mg, 0.50 mmol) and MnCl2 (318 mg, 2.53 mmol) in anhydrous DMF (50 mL) was magnetically stirred and heated to 145° C. for 1 h then exposed to a stream of air for 2 h. The reaction mixture was cooled to room temperature overnight under a stream of air. Evaporation of DMF provided a crude solid mixture which was adsorbed onto silica gel (2 g). Purification by column chromatography (gradient elution with 0-5% MeOH/CH2Cl2) provided porphyrins 41 (170 mg) and 42 (10 mg) as solids. For porphyrin 41: mp 200-210° C.; UV-vis λmax=456.0 nm, ε=1.4×105 L/cm-mol; FAB MS m/z=763 [C40H44MnN4O8]+. For porphyrin 42: mp 200-205° C.; UV-vis λmax=459.5 nm, ε=7.2×104 L/cm-mol; FAB MS m/z=707, [C36H36MnN4O8]+.

Workup

temperatureThe reaction mixture was cooled to room temperature overnight under a stream of air
customEvaporation of DMF
customprovided a crude solid mixture which
customPurification
washby column chromatography (gradient elution with 0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-86b7719936c74b4cb866912d18e6d9d2
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479477B1

Reaction notes

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