Formic Acid → 2-Methyl-4-nitrophenylformamide

HRID 1029861Notes

Reaction equation

HRID 1029861 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[CH3:11][C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=1[NH2:14]>C1COCC1>[CH:5]([NH:14][C:13]1[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:12]=1[CH3:11])=[O:7]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 74412-Methyl-4-nitroanilineHCID 7918Acetic Anhydride

Product 1

HCID 35570182-Methyl-4-nitrophenylformamideYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

25 g (0.26 mol) of acetic anhydride were cooled to 0° C. under nitrogen. 15 g (0.32 mol) of formic acid were added dropwise at this temperature. The resultant mixture was then allowed to melt, and was then warmed to from 50 to 60° C. over the course of two hours. The mixture was then cooled to room temperature, and 20 ml of dry tetrahydrofuran were added, and the resultant mixture was again cooled to 0° C. A suspension of 15.2 g (0.1 mol) of 2-methyl-4-nitroaniline in 100 ml of THF was then added dropwise to this mixture, and the resultant mixture was left at 0° C. for one hour and then warmed to room temperature. The resultant yellow precipitate was filtered off with suction, washed with water and dried at 50° C. under reduced pressure, to give 13.9 g of N-formyl-2-methyl-4-nitroaniline (yield: 77%). The product had the same physical/chemical properties as that prepared in the above-described manner (compare section 1.1).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. additionwas then added dropwise to this mixture
  3. temperaturewarmed to room temperature
  4. filtrationThe resultant yellow precipitate was filtered off with suction
  5. washwashed with water
  6. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-16af496a136846438a05644efad81edc
Source dataset
uspto-grants-1992_04
Patent number
US05103060

Reaction notes

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