Formic Acid → Formaldehyde

HRID 551718Notes

Reaction equation

HRID 551718 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH:8](O)=[O:9]>>[C:5]12[CH:6]=[C:2]3[N:1]=[C:5]([CH:4]=[CH:3]3)[CH:6]=[C:2]3[NH:1][C:5]([CH:4]=[CH:3]3)=[CH:6][C:2]3=[N:1][C:5]([CH:4]=[CH:3]3)=[CH:6][C:2]([NH:1]1)=[CH:3][CH:4]=2.[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH2:8]=[O:9]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 13854Pyrrole-2-carboxaldehyde

Product 3

HCID 712FormaldehydeHCID 8027PyrroleHCID 13770524121H,22H-Porphine

Procedure

The reported methods for the synthesis of porphine over the past 70 years are summarized in Table 1. Fischer and Gleim obtained 17 mg of porphine by prolonged heating of 20 g of pyrrole-2-carboxaldehyde in formic acid.6 In the same era, Rothemund obtained porphine from pyrrole and formaldehyde, albeit in very low yield (0.02%).7 The yield was increased to 0.9% by slow addition of pyrrole and formaldehyde to propionic acid.8

Sources & evidence

ORD record
ord-052c7163564f43058aed0e0fd4636338
Source dataset
uspto-grants-2011_05
Patent number
US07947829B2

Reaction notes

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