Formic Acid → HCID 86621475, compound

HRID 734633Notes

Reaction equation

HRID 734633 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]1[NH:13][CH:14]=[C:15]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[C:16]=1[C:17]([NH2:19])=[O:18].O>C(O)C>[CH:1]([NH:11][C:12]1[NH:13][CH:14]=[C:15]([C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[C:16]=1[C:17]([NH2:19])=[O:18])=[O:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 57845538HCID 57845538, compound

Product 1

HCID 86621475HCID 86621475, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2 cm3 (52.9 mmol) of formic acid in 5 cm3 (52.9 mmol) of acetic anhydride is added, at a temperature close to 25° C., to a solution of 0.3 g (1.21 mmol) of 2-amino-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide in 5 cm3 of absolute ethanol. After stirring for 2 hours at this temperature, the reaction medium is poured into 100 cm3 of water. The suspension is then filtered. The solid is drained, dried to give 0.257 g of 2-formylamino-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide in the form of a green powder. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm), from 6.22 to 8.53 (very broad m, 2H); 6.78 (d, J=3.0 Hz, 1H); 7.64 (d, J=9.0 Hz, 2H); 8.19 (d, J=9.0 Hz, 2H); 8.32 (d, J=1.5 Hz, 1H); 10.55 (broad s, 1H); 11.6 (broad s, 1H).

Workup

  1. filtrationThe suspension is then filtered
  2. customdried

Sources & evidence

ORD record
ord-af2a765d2a3940f3acfa85049960f9fc
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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