Formic Acid → N-(2-methoxy-5-nitrophenyl)formamide

HRID 2392665Notes

Reaction equation

HRID 2392665 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:14]=1[NH2:15]>C1COCC1>[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:14]=1[NH:15][CH:1]=[O:3]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 74472-Methoxy-5-nitroanilineHCID 7918Acetic Anhydride

Product 1

HCID 264510N-(2-methoxy-5-nitrophenyl)formamideYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of formic acid (0.45 ml, 0.012 mole) and acetic anhydride (1.06 ml, 0.011 mole) was stirred at 55° C. under Ar for 2 h, and cooled to room temperature. Dry THF (10 ml) was added. To this solution was added 2-methoxy-5-nitroaniline (0.69 g, 0.004 mole). After stirring for 1 h, the suspension was evaporated in vacuo to leave the title compound as a brown solid (0.80 g, 99%).

Workup

  1. temperaturecooled to room temperature
  2. stirringAfter stirring for 1 h
  3. customthe suspension was evaporated in vacuo

Sources & evidence

ORD record
ord-7c7e3a1ae1ef4d34921aa31fbc44a50f
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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