Pyridine → N-(2-Hydroxy-5-nitrophenyl)formamide

HRID 643937Notes

Reaction equation

HRID 643937 reaction equation
[C:1](OC(=O)C)(=[O:3])C.N1C=CC=CC=1.[NH2:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[OH:24]>C(O)=O>[OH:24][C:16]1[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=1[NH:14][CH:1]=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 4089953N-(2-Hydroxy-5-nitrophenyl)formamide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

To a stirred mixture of formic acid (20.7 g, 0.449 mol), acetic anhydride (32.0 g, 0.313 mol) and pyridine (37 g, 0.468 mol) is added at ambient temperature 2-amino-4-nitrophenol (24.0 g, 0.156 mol) in 15 mL of formic acid. Stirring is continued for 18 h. The solid formed is separated by suction filtration, washed with aqueous sodium bicarbonate, water, DCM and hexanes. After air drying for 18 h, N-(2-hydroxy-5-nitrophenyl)-formamide is obtained as a light green solid: (M−H)−=181.1.

Workup

  1. customThe solid formed
  2. customis separated by suction filtration
  3. washwashed with aqueous sodium bicarbonate, water, DCM and hexanes
  4. customAfter air drying for 18 h

Sources & evidence

ORD record
ord-f5997bc49a2744a384f6bfd251574829
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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