Formic Acid → Formaldehyde

HRID 20198

Reaction equation

HRID 20198 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-663bc20c00f64cb7a43ef897fbd917f0
Source dataset
uspto-grants-2010_06
Patent number
US07745618B2

Linked notes

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