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

HRID 626239Notes

Reaction equation

HRID 626239 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][NH2:15]>>[CH3:14][NH:15][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 73204-Chloro-3-nitrobenzoic acid

Product 1

HCID 2834754-(Methylamino)-3-nitrobenzoic acid

Procedure

A solution of 4-chloro-3-nitrobenzoic acid (30 g, 1.0 eq) in 200 mL CH3NH2 (aq) was stirred at 100° C. for 14 h, cooled, and concentrated in vacuo. The residue was poured into 200 mL 2N HCl (aq) at ° C. The suspension was filtered and washed with water to give the product as yellow solid (quant). 1H NMR (400 MHz, DMSO-d6) δ 8.58 (d, J=2.0 Hz, 1H), 8.51 (d, J=5.2 Hz, 1H), 7.95 (dd, J=9.2 Hz, 2.0 Hz, 1H), 7.02 (d, J=9.2 Hz, 1H), 2.98 (s, 3H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. additionThe residue was poured into 200 mL 2N HCl (aq) at ° C
  4. filtrationThe suspension was filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-c9c8eadfcd4744cc9a76dfdd54c5c74d
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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