Formic Acid → 3-Nitro-4-formamidobenzaldehyde

HRID 2082810Notes

Reaction equation

HRID 2082810 reaction equation
[CH:1]([OH:3])=O.[N+:4]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[NH2:15])[CH:10]=[O:11])([O-:6])=[O:5].C(OC(=O)C)(=O)C>O>[N+:4]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[NH:15][CH:1]=[O:3])[CH:10]=[O:11])([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 132377034-Amino-3-nitrobenzaldehyde

Product 1

HCID 203400463-Nitro-4-formamidobenzaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 56.6 ml (1.50 mol) of HCOOH was added 24.9 g (150 mmol) of 3-nitro-4-aminobenzaldehyde. The solution was heated to reflux, 28.4 ml (300 mmol) of acetic anhydride was added dropwise and the solution was refluxed for 30 minutes. The resulting suspension was cooled and poured into 400 ml of cold H2O with rapid stirring. The product was filtered, air dried, and recrystallized from isopropanol to yield 23.2 g (80%) of 3-nitro-4-formamidobenzaldehyde as a bright yellow powder: melting point = 183°-191°.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperaturethe solution was refluxed for 30 minutes
  4. temperatureThe resulting suspension was cooled
  5. filtrationThe product was filtered
  6. customair dried
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-708a7115481f43c0b061d2790bf68390
Source dataset
uspto-grants-1978_04
Patent number
US04082847

Reaction notes

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