Methylamine → 4-(Methylamino)-3-nitrobenzoic acid

HRID 1410207Notes

Reaction equation

HRID 1410207 reaction equation
[CH3:1]N.[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)[C:9]([OH:11])=[O:10])([O-:5])=[O:4]>CCO>[CH3:1][NH:15][C:14]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:3]([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 107093,4-Dinitrobenzoic acid

Product 1

HCID 2834754-(Methylamino)-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

TEA (13 mL) and methylamine (2 M in MeOH, 35 mL, 70 mmol) was added to 3,4-dinitrobenzoic acid (10 g, 47.2 mmol) in EtOH (50 mL) at rt. After 24 h at rt the mixture was concentrated and H2O was added to the residue. The mixture was filtered and acidified with AcOH. The solids were collected and dried to give the sub-title compound. Yield: 7.5 g (81%).

Workup

  1. concentrationAfter 24 h at rt the mixture was concentrated
  2. additionH2O was added to the residue
  3. filtrationThe mixture was filtered
  4. customThe solids were collected
  5. customdried

Sources & evidence

ORD record
ord-8c0b77e8fea4451cad0c3069020a5c5e
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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